4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)methanol

A solution of BH3 (1 M in THF, 720 mL, 0.7194 mol) was slowly added to 4-bromo-2-methyl benzoic acid (51.57 g, 0.2398 mol) at 0° C. The ice-bath was removed and the mixture was stirred overnight at room temperature. The reaction mixture was cooled to 0° C. and water was slowly added. The reaction mixture was then stirred at room temperature for 30 minutes. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with NaHCO3 (saturated solution), water and brine; dried over MgSO4, filtered and evaporated under reduced pressure affording (4-bromo-2-methyl-phenyl)-methanol, which was used directly in step 2 without further purification.

1. customThe ice-bath was removed
2. temperatureThe reaction mixture was cooled to 0° C.
3. additionwater was slowly added
4. stirringThe reaction mixture was then stirred at room temperature for 30 minutes
5. extractionThe resulting mixture was extracted with EtOAc
6. washthe combined organic extracts were washed with NaHCO3 (saturated solution), water and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-fdf853b3d8cc4230882f1ebff7f3a9bc

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776910B2