Bromine → 2-Bromo-4-(trifluoromethoxy)phenol

A solution of 1.78 g (10.0 mmol) of 4-trifluoromethoxyphenol in 5 mL of CH2Cl2 at 0° C. was treated with a solution of 2.20 g (14.0 mmol) of bromine in 5 mL of CH2Cl2. The cooling bath was removed and the resulting mixture was stirred at rt for 20 h. The reaction quenched with 5% aqueous Na2S2O3 and the resulting mixture was partitioned between 150 mL of ether and 150 mL of H2O. The layers were separated; the organic layer was dried over MgSO4 and concentrated in vacuo. Flash chromatography on 125 g of silica gel using 9:1 v/v hexanes/CH2Cl2 as the eluant afforded 1.45 g (56%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ 5.50 (s, 1H), 7.02 (d, J=9.0, 1H), 7.12 (dd, J=9.0, 2.0, 1H), 7.37 (d, J=2.0, 1H).

1. customThe cooling bath was removed
2. customThe reaction quenched with 5% aqueous Na2S2O3
3. customthe resulting mixture was partitioned between 150 mL of ether and 150 mL of H2O
4. customThe layers were separated
5. dry with materialthe organic layer was dried over MgSO4
6. concentrationconcentrated in vacuo

ORD record

ord-6cab574601a743ca88b6ffc9c51f1de9

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05877191