5-Bromo-2-methylbenzoic acid → (5-Bromo-2-methylphenyl)methanol

To a solution of 5-bromo-2-methylbenzoic acid (25.00 g, 116 mmol) in THF (250 mL) at 0° C. was added borane dimethyl sulfide complex (2.0 M in THF, 87 mL, 174 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 hours. The mixture was cooled to 0° C. and quenched by dropwise addition of MeOH (100 mL) within 15 minutes. The mixture was stirred at 0° C. for 15 minutes and concentrated. The residue was taken up in EtOAc and washed with 1 M HCl, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated to give INT 29.

1. temperatureThe mixture was cooled to 0° C.
2. customquenched by dropwise addition of MeOH (100 mL) within 15 minutes
3. stirringThe mixture was stirred at 0° C. for 15 minutes
4. concentrationconcentrated
5. washwashed with 1 M HCl, saturated aqueous NaHCO3 and brine
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto give INT 29

ORD record

ord-b00549209c3b4be8a0273610f0f2a3f6

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791100B2