Methyl 5-bromo-2-methoxy-3-methylbenzoate → (5-Bromo-2-methoxy-3-methylphenyl)methanol

Temperature

-78 °C

Methyl 5-bromo-2-methoxy-3-methylbenzoate (2.26 g, 8.7 mmol) was dissolved in methylene chloride (30 mL), cooled to −78° C., and treated with diisobutylaluminum hydride (1 M in methylene chloride, 26.1 mL, 26.1 mmol). After stirring at −78° C. for 1 h the reaction was quenched by a few drops of methanol (until no bubbling was observed) followed by addition of excess saturated sodium potassium tartarate (2 mL). The reaction was stirred at room temperature overnight. The layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate, and concentrated to afford 2.0 g (quant). 1H-NMR (CDCl3, 500 MHz) δ 7.30-7.31 (m, 1H), 7.21-7.22 (m, 1H), 4.62 (s, 2H), 3.71 (s, 3H), 2.23 (s, 3H).

1. customwas quenched by a few drops of methanol (until no bubbling
2. additionfollowed by addition of excess saturated sodium potassium tartarate (2 mL)
3. stirringThe reaction was stirred at room temperature overnight
4. customThe layers were separated
5. washthe organic layer washed with brine (2×)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customto afford 2.0 g (quant)

ORD record

ord-e4f14978e1474270bcdbfeae1f894956

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383821B2