Methanol → 3-Bromo-2-methoxybenzenemethanol

LiBH4 (5.00 g, 0.23 mmol) was added to a solution of 3-bromo-2-methoxy-benzoic acid methyl ester (10.50 g, 42.80 mmol) in Et2O at 0° C. The reaction mixture was stirred for 5 minutes, MeOH (8.70 mL, 0.22 mmol) was added in a dropwise fashion. The reaction mixture was then stirred for 30 minutes, and was quenched into 1N NaOH. The resulting solution was extracted with Et2O (3×200 mL) and the combined organic phases were washed with brine (1×150 mL), dried over MgSO4 and concentrated to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 1.68 (t, J=5.86 Hz, 1H), 3.90 (s, 3H), 4.61 (d, J=5.86 Hz, 2H), 6.89 (d, J=8.50 Hz, 1H), 7.25-7.30 (m, J=2.00 Hz, 1H), 7.57 (d, J=2.05 Hz, 1H).

1. stirringThe reaction mixture was then stirred for 30 minutes
2. customwas quenched into 1N NaOH
3. extractionThe resulting solution was extracted with Et2O (3×200 mL)
4. washthe combined organic phases were washed with brine (1×150 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD record

ord-bf8ed33c063f48eb988d306d85c06d7e

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557853B2