2-Chloro-6-fluorotoluene → 3-Bromo-2-chloro-6-fluorotoluene

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 (10%, 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, 98%) containing 15% 3-bromo-5-chloro-2-fluorotoluene (calc. by 1H-NMR). The compound was used in the next step without further purification.

1. customthe reaction mixture transferred to a separation funnel
2. washwashed with a sodium thiosulphate solution (10%, 30 mL) until it
3. customThe layers were separated
4. washthe organic layer was washed with sat. sodium hydrogen carbonate (30 mL)
5. customdried
6. customevaporated

ORD record

ord-b72b1655e8b94d74a98265ac2f5fe9f0

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585877B2