反应详情

A mixture of methyl 3,5-dibromo-4-methylbenzoate (15 g, 48.706 mmol), NaBH4 (5.53 g, 146.18 mmol) and absolute ethanol (175 mL) was heated to reflux for 4 h. The mixture was cooled, followed by acidification with 2N HCl. The solids were filtered through celite and rinsed with EtOAc. The filtrate was poured onto water and extracted. The organic layer was washed with brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded (3,5-dibromo-4-methyl-phenyl)-methanol (9.94 g) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.48 (s, 3H), 4.45 (d, 2H), 5.38 (t, 1H), 7.57 (s, 2H) ppm.

1. temperaturewas heated
2. temperatureto reflux for 4 h
3. temperatureThe mixture was cooled
4. filtrationThe solids were filtered through celite
5. washrinsed with EtOAc
6. additionThe filtrate was poured onto water
7. extractionextracted
8. washThe organic layer was washed with brine
9. dry with materialdried (Na2SO4)