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2 reactions in Reaxys
2017-09-22 21h:12m:11s (EST)
Cl
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Br
F
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2017-09-22 21:14:50
Br
Cl
Cl
F
Br
F
F
Cl
Rx-ID: 29451532 View in Reaxys 1/2 Yield
Conditions & References With bromine, iron, T= 20 °C Schlienger, Nathalie; Lund, Birgitte W.; Pawlas, Jan; Badalassi, Fabrizio; Bertozzi, Fabio; Lewinsky, Rasmus; Fejzic, Alma; Thygesen, Mikkel B.; Tabatabaei, Ali; Bradley, Stefania Risso; Gardell, Luis R.; Piu, Fabrice; Olsson, Roger; Journal of Medicinal Chemistry; vol. 52; nb. 22; (2009); p. 7186 - 7191 View in Reaxys
Cl
Cl
F
Br
F
Rx-ID: 23841578 View in Reaxys 2/2 Yield ~ 98 %
Conditions & References 2 :Example 2 3-Bromo-2-chloro-6-fluorotoluene (165RL91) 2-chloro-6-fluorotoluene (5.00 g, 34.6 mmol) and iron (0.1 g, 0.17 mmol) was stirred in a 100 mL flask. Bromine (6.08 g, 38.1 mmol) was added slowly in 3 portions with 1 min between each addition. The reaction was stirred for additional 15 min. Then dichloromethane (50 ml) was added, the reaction mixture transferred to a separation funnel and washed with a sodium thiosulphate solution (10percent, 30 mL) until it had turned colorless. The layers were separated and the organic layer was washed with sat. sodium hydrogen carbonate (30 mL), dried and evaporated to give the title compound as a colorless oil (7.57 g, 98percent) containing 15percent 3-bromo-5-chloro-2-fluorotoluene (calc. by 1H-NMR). The compound was used in the next step without further purification. GC/MS m/z 222 [M+H]+. 1H-NMR (CDCl3, 300 MHz) δ 7.53 (dd, 1H, J=5.5, 8.6, Ar-H), 7.07 (t, 1H, J=8.6, Ar-H), 2.35 (d, 3H, J=2.3, CH3). With bromine, iron, Time= 0.25h Patent; Schlienger, Nathalie; Thygesen, Mikkel Boas; Pawlas, Jan; Badalassi, Fabrizio; Lewinsky, Rasmus; Lund, Birgitte Winther; Olsson, Roger; US2006/160845; (2006); (A1) English View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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2017-09-22 21:14:50