Reacción #42399

Ecuación de reacción

3-bromo-5-(methoxycarbonyl)benzoic acid

borane dimethyl sulfide

→

title compound

Methyl 3-bromo-5-(hydroxymethyl)benzoate

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture is quenched with methanol (50 mL)
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   OtroPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Procedimiento

To an ice-cold, stirred solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (5.0 g, 19.3 mmol) in tetrahydrofuran (77.2 mL) is added borane dimethyl sulfide complex (10.6 mL, 2.0 M tetrahydrofuran, 21.1 mmol). The reaction mixture is heated at 50° C. for 2 h. The reaction mixture is quenched with methanol (50 mL) and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H), 7.90 (s, 1H), 7.69 (s, 1H), 4.69 (s, 1H), 3.91 (s, 3H), 2.83 (br s, 1H).

Fuente