Tetrabutylammonium Fluoride → 3-Bromo-6-chloro-2-(3-hydroxypropyl)-5-(4-methoxybenzyl)phenol
Reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([O:12][Si](C(C)(C)C)(C)C)[C:5]([Cl:20])=[C:4]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([OH:12])[C:5]([Cl:20])=[C:4]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of alcohol 187 (1.73 g, 3.46 mmol) in THF (28 mL) was added TBAF (1M in THF, 7.0 mL, 6.92 mmol) at 0° C. The mixture was stirred for 1 hr at rt. The mixture was extracted with EtOAc/aq. sat'd NH4Cl solution (500 mL/50 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 188 (1.19 g, 89%).