Benzylmagnesium chloride [BnMgCl]

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Query Query Mg

1. Query

Cl

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Date

15 reactions in Reaxys

2016-06-29 20h:54m:19s (EST)

15 reactions in Reaxys

2016-06-29 20h:54m:45s (EST)

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Cl

Mg

Cl

Rx-ID: 605640 View in Reaxys 1/15 Yield

Conditions & References

99 %

2 :The reaction for the preparation of benzylmagnesium chloride was carried out as in Example 1.Benzyl chloride was fed in a mixture of solvents: THF and methyl-tert-butyl ether (1:1; v/v) as a 10percent solution. When the operation of the reaction system stabilised, a solution of the Grignard compound was obtained with a 99percent yield. The product did not contain diphenylethane. With bromine, magnesium in tetrahydrofuran, tert-butyl methyl ether, T= 20 - 35 °C , Inert atmosphere, Product distribution / selectivity Patent; ZAKLADY FARMACEUTYCZNE POLPHARMA SA; SZEJA, Wieslaw; HELMAN, Jan; KIRAGA, Krzysztof; DERFLA, Sebastian; WO2010/117285; (2010); (A2) English View in Reaxys

95 %

With magnesium in tetrahydrofuran, T= 20 - 23 °C Benkeser, Robert A.; Snyder, Dudley C.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1243 - 1249 View in Reaxys

90 %

With polymer supported 'magnesium(anthracene)' Harvey, Stephen; Raston, Colin L.; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 652 - 653 View in Reaxys Gilman; Vanderwal; Bulletin de la Societe Chimique de France; vol. <4> 45; (1929); p. 642 View in Reaxys With magnesium in diethyl ether Wagner,B.O.; Hammond,G.S.; Journal of Organometallic Chemistry; vol. 85; (1975); p. 1 - 14 View in Reaxys Berrier, C.; Jacquesy, J. C.; Gesson, J. P.; Renoux, A.; Tetrahedron; vol. 40; nb. 11; (1984); p. 1983 - 1994 View in Reaxys With magnesium in diethyl ether, T= 0 °C Baker, Karen V.; Brown, John M.; Hughes, Nigel; Skarnulis, A. Jerome; Sexton, Ann; Journal of Organic Chemistry; vol. 56; nb. 2; (1991); p. 698 - 703 View in Reaxys With magnesium in diethyl ether, Time= 3h, T= 45 °C Katritzky, Alan R.; Hughes, Craig V.; Rachwal, Stanislaw; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 1579 - 1588 View in Reaxys With magnesium in tetrahydrofuran, T= 25 °C , Inert atmosphere, Schlenk technique, Glovebox Rong, Yi; Al-Harbi, Ahmed; Parkin, Gerard; Organometallics; vol. 31; nb. 23; (2012); p. 8208 - 8217 View in Reaxys

O

magnesium

Cl

Mg

Cl

Rx-ID: 6163092 View in Reaxys 2/15 Yield

Conditions & References Klages; Heilmann; Chemische Berichte; vol. 37; (1904); p. 1452 View in Reaxys Klages; Chemische Berichte; vol. 38; (1905); p. 2220 Anm. 5

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View in Reaxys Held; Chemische Berichte; vol. 37; (1904); p. 455; Chemische Berichte; vol. 38; (1905); p. 1682 View in Reaxys O

Cl

Mg

S

Rx-ID: 21441960 View in Reaxys 3/15 Yield

Conditions & References Reaction Steps: 2 1: Se / toluene / 1.5 h / Heating 2: Raney nickel / ethanol / Heating With selenium, nickel in ethanol, toluene Nakayama, Juzo; Akimoto, Keiichi; Niijima, Jun; Hoshino, Masamatsu; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4423 - 4426 View in Reaxys

glycosyl bromide

Cl

Mg

Rx-ID: 24520510 View in Reaxys 4/15 Yield

Conditions & References 4 : 4-(Retinamido)benzyl-C-glucuronide The p-nitrobenzoic acid was removed by filtration and the filtrate was concentrated to give the crude glycosyl bromide which was dissolved in 50 ml of ether and added to benzylmagnesium chloride prepared from 600 mg (0.0247 g-atom) of magnesium and 2.8 ml (24.3 mmol) benzyl chloride. The mixture was heated at reflux for 4 hours then poured into 100 ml of water containing 5 ml of acetic acid. The mixture was shaken and separated. The ether layer was washed twice with 50 ml saturated NaHCO3, once with 50 ml brine, dried using MgSO4, and concentrated. The residue was dissolved in 80 ml glacial acetic acid containing 0.1 g of 10percent palladium on carbon and shaken under 40 PSI of hydrogen for 19 hours. The catalyst was removed by filtration and the filtrate was concentrated to dryness. The residue was acetylated with 30 ml of pyridine and 30 ml of acetic anhydride over 16 hours. The reaction was poured into 100 ml of water and extracted twice with 50 ml of ether. Patent; Ohio State Research Foundation; US5516792; (1996); (A1) English View in Reaxys

Cl

Mg

Rx-ID: 24904617 View in Reaxys 5/15 Yield

Conditions & References 31 : EXAMPLE 31 EXAMPLE 31 2,5-Dimethyl-6-phenyl-1,2,4-triazin-3(2H)-one (3.2 g) was added to a stirred solution of benzylmagnesium chloride prepared from benzyl chloride (9.99 g) and magnesium turnings (1.92 g) in diethyl ether (48 ml) at room temperature. Patent; Fujisawa Pharmaceutical Co., Ltd.; US4616014; (1986); (A1) English View in Reaxys

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Cl

Mg

Br

Rx-ID: 37573812 View in Reaxys 6/15 Yield

Conditions & References With iodine, magnesium in tetrahydrofuran, Time= 0.5h, T= 20 - 50 °C , Inert atmosphere Dhakal, Ramesh C.; Dieter, R. Karl; Organic Letters; vol. 16; nb. 5; (2014); p. 1362 - 1365 View in Reaxys

Cl

Mg

Cl

Rx-ID: 2697585 View in Reaxys 7/15 Yield

Conditions & References With magnesium 9,10-dimethylanthracene * 3 THF in tetrahydrofuran, Time= 3h, Yield given. Yields of byproduct given Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg; Seevogel, Klaus; Treber, Joachim; Chemische Berichte; vol. 123; nb. 7; (1990); p. 1529 - 1535 View in Reaxys

(v5) (v5)(v5) (v5)

– Br(v10) Fe

N+

Mg

Cl

(v5) (v5)

(v5) (v5)

(v5)

N

(v10)

(v5)

(v5) (v5) N (v5)

Cl

Fe (v5) (v5)

Mg

(v5)

Rx-ID: 26698925 View in Reaxys 8/15 Yield

Conditions & References

70 %, 61 %, 10 %

With CoCl2 Perevalova, E. G.; Ustynyuk, Yu. A.; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 1631 1635; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1963); p. 1776 - 1782 ; (from Gmelin) View in Reaxys

70 %, 61 %, 10 %

With CoCl2 vol. Fe: Org.Verb.A4; 5.1.4.1.4.3, page 80 - 89 ; (from Gmelin) View in Reaxys

O Se

O

Cl

Mg

Rx-ID: 2568868 View in Reaxys 9/15 Yield 57 %

Conditions & References With nickel in ethanol, Heating

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Nakayama, Juzo; Akimoto, Keiichi; Niijima, Jun; Hoshino, Masamatsu; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4423 - 4426 View in Reaxys OH

Cl

O Cl

Mg

Cl

Rx-ID: 25123774 View in Reaxys 10/15 Yield

Conditions & References Preparation of the starting material STR71 Preparation of the starting material STR71 115.3 g (0.5 mol) of 4-phenylphenacyl chloride are added portions to a solution of benzyl-magnesium chloride, obtained from 24.3 g (1 mol) of magnesium and 115 ml (1 mol) of benzyl chloride in 150 ml of diethyl ether. The reaction mixture is warmed under reflux for 90 minutes and then poured onto aqueous ammonium chloride solution. The ether phase is separated off, washed with water, dried over sodium sulphate and concentrated. The oil which remains is made to crystallise by stirring with petroleum ether. 50 g (31percent of theory) of 2-(4-biphenylyl)-3-chloro-1-phenylpropan-2-ol of melting point 96° C. are obtained. Patent; Bayer Aktiengesellschaft; US4381306; (1983); (A1) English View in Reaxys

O 3

Mg

Cl

Cl

Mg

Rx-ID: 2695617 View in Reaxys 11/15 Yield

Conditions & References in tetrahydrofuran, Time= 3h, Ambient temperature, Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg; Chemische Berichte; vol. 123; nb. 7; (1990); p. 1507 - 1515 View in Reaxys

O 3

Mg

Cl

Cl

Mg

Rx-ID: 2695618 View in Reaxys 12/15 Yield

Conditions & References in tetrahydrofuran, Time= 3h, Ambient temperature, Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts

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Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg; Chemische Berichte; vol. 123; nb. 7; (1990); p. 1507 - 1515 View in Reaxys

O 3

Mg

Cl

Cl

Mg

Rx-ID: 2695619 View in Reaxys 13/15 Yield

Conditions & References in tetrahydrofuran, Time= 3h, Ambient temperature, Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg; Chemische Berichte; vol. 123; nb. 7; (1990); p. 1507 - 1515 View in Reaxys

Cl

Mg

Cl

Rx-ID: 2697597 View in Reaxys 14/15 Yield

Conditions & References With magnesium anthracene * 3 THF in diethyl ether, Time= 1h, Ambient temperature, Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts Bogdanovic, Borislav; Janke, Nikolaus; Kinzelmann, Hans-Georg; Chemische Berichte; vol. 123; nb. 7; (1990); p. 1507 - 1515 View in Reaxys

O O S O

O

Cl

Mg

NH 2

Rx-ID: 24520511 View in Reaxys 15/15 Yield

Conditions & References 7 : Synthesis of sulfamic acid(phenylacetyl)-2,6-bis(1-methylethyl)phenyl ester EXAMPLE 7 Synthesis of sulfamic acid(phenylacetyl)-2,6-bis(1-methylethyl)phenyl ester This compound was prepared in the same manner as the title compound of Example 5, except that 2,4,6-triisopropylbenzyl magnesium bromide was replaced with benzylmagnesium chloride (commercially available), mp 150°-152° C. Patent; Warner-Lambert Company; US5491172; (1996); (A1) English View in Reaxys

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