4-Bromo-3-(butyloxy)benzoic acid → (4-Bromo-3-(butyloxy)phenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A solution of 20.1 (0.68 g, 2490 μmol) in THF (5 mL) was treated with borane THF complex (4979 μL, 4979 μmol) and stirred overnight at 65° C. The reaction mixture was quenched with MeOH, diluted with EtOAc, and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by combiflash (10 to 50% EtOAc/hexanes) yielding 20.2 (659.3 mg, 102% yield).
Workup
- customThe reaction mixture was quenched with MeOH
- additiondiluted with EtOAc
- washwashed with water and brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
- customThe crude product was purified by combiflash (10 to 50% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-742b83af6866476c8c5c823506a9982a
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030354B2
Reaction notes
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