Water → (2-Bromo-5-methoxyphenyl)methanol

5-Methoxy-2-bromobenzoic acid (85 g, 0.37 mol) is dissolved in anhydrous THF (100 mL) and cooled in an ice-salt bath until the temperature reaches −5° C. Borane-THF complex is added dropwise as a 1.0 M solution in THF (736 mL, 0.74 mol) at −5° C. After addition is complete, the reaction mixture is slowly warmed to room temperature and stirred for 12 hours. Water (40 mL) is slowly added dropwise and the reaction mixture stirred for 30 minutes. Additional water (350 mL) is added and the mixture is concentrated by rotary evaporator to remove most of the THF. The remaining material is extracted with EtOAc (800 mL). The organic layer is washed with saturated NaHCO3 (500 mL), brine (250 mL) and then dried (Na2SO4). Upon removal of the solvent by rotary evaporator, 5-methoxy-2-bromobenzyl alcohol is obtained as a white solid.

1. temperaturecooled in an ice-salt bath until the temperature
2. customreaches −5° C
3. additionAfter addition
4. stirringthe reaction mixture stirred for 30 minutes
5. concentrationthe mixture is concentrated by rotary evaporator
6. customto remove most of the THF
7. extractionThe remaining material is extracted with EtOAc (800 mL)
8. washThe organic layer is washed with saturated NaHCO3 (500 mL), brine (250 mL)
9. dry with materialdried (Na2SO4)
10. customUpon removal of the solvent
11. customby rotary evaporator

ORD record

ord-6802e35a3b354c449e509d708a964ac6

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07202364B2