4-Bromo-2-fluorobenzaldehyde → 1-(4-Bromo-2-fluorophenyl)ethanol

To a solution of 4-bromo-2-fluorobenzaldehyde (2.01 g, 9.9 mmol) in tetrahydrofuran (20 mL) was dropped methylmagnesium bromide (10 mmol, 1N in tetrahydrofuran) and the mixture was stirred at room temperature for 30 minutes. TLC showed all starting material was consumed, then mixture was quenched with aqueous ammonium chloride (1N, 5 mL). To the mixture, water (50 mL) was added and extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give the product 1-(4-bromo-2-fluorophenyl)ethanol as colorless oil (2.0 g, 92%). 1H NMR (300 MHz, CDCl3): δ 7.40-7.19 (m, 3H), 5.16 (q, J=6.3 Hz, 1H), 1.76 (s, 1H), 1.49 (d, J=6.3 Hz, 3H).

1. customwas consumed
2. custommixture was quenched with aqueous ammonium chloride (1N, 5 mL)
3. additionTo the mixture, water (50 mL) was added
4. extractionextracted with dichloromethane (2*50 mL)
5. customThe combined organic phase was separated
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1)

ORD record

ord-e24389f3e6a646ae96706beabe5eff2c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206128B2