Methyl 4-bromo-3-methylbenzoate → (4-Bromo-3-methylphenyl)methanol

A solution of methyl 4-bromo-3-methylbenzoate (2.0 g, 8.7 mmol) in dry THF (10 mL) was added to an ice-cooled suspension of lithium aluminiumhydride (400 mg, 10.4 mmol) in dry THF (30 mL). After addition, the mixture was warmed to room temperature and then stirred for 3 h. The excess lithium aluminiumhydride was quenched by successive addition of water (0.4 mL), 15% NaOHaq (0.4 mL), and water (1.2 mL) under ice cooling. The insoluble material appeared was removed by filtration (celite), and the precipitate was washed by AcOEt (20 mL×5). The combined filtrates were washed with brine (50 mL) and then dried over Na2SO4. The solvent was evaporated, and the obtained product (1.6 g, 100%) was used for next step without further purification. 1H-NMR (CDCl3, 400 MHz): δ7.53 (1H, d, J=8.1 Hz), 7.26 (1H, d, J=1.5 Hz), 6.40 (1H, dd, J=8.1, 1.5 Hz), 4.68 (2H, s), 2.44 (3H, s).

1. temperaturecooled
2. additionAfter addition
3. customThe excess lithium aluminiumhydride was quenched by successive addition of water (0.4 mL), 15% NaOHaq (0.4 mL), and water (1.2 mL) under ice cooling
4. customThe insoluble material appeared was removed by filtration (celite)
5. washthe precipitate was washed by AcOEt (20 mL×5)
6. washThe combined filtrates were washed with brine (50 mL)
7. dry with materialdried over Na2SO4
8. customThe solvent was evaporated
9. customthe obtained product (1.6 g, 100%) was used for next step without further purification

ORD record

ord-d85fdced7daa4f9c9d957852f869f8e5

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865914B2