N-(2,6-Difluoro-3-hydroxy-phenyl)-2, 3-dimethyl-5-phenyl-benzamide → 3-[(2,3-Dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenol
Reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[C:14]([CH3:24])[C:13]=1[CH3:25]>C1COCC1>[CH3:25][C:13]1[C:14]([CH3:24])=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:17][C:12]=1[CH2:11][NH:10][C:3]1[C:2]([F:1])=[C:7]([OH:8])[CH:6]=[CH:5][C:4]=1[F:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-2,3-dimethyl-5-phenyl-benzamide (210 mg, 0.6 mmol, 1.0 eq) in THF (4 mL) at 0° C. was added dropwise a solution of BH3 (1M in THF, 3.6 mL, 3.6 mmol, 6.0 eq). The reaction mixture was heated at 60° C. for 5 h, then cooled and quenched by addition of water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:0 to 10:1) to give the title compound as colorless oil (120 mg, 60%).