(2-Bromo-4-phenylphenyl) acetate → 3-Bromo-4'-hydroxybiphenyl
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16]C=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1OC(=O)C.[CH3:18][O-:19].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:18]([OH:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1.07 g (3.67 mmole) of 3-bromo-4-acetoxybiphenyl in 10 mL methanol at ambient temperature under a nitrogen atmosphere was added 0.92 mL of 4.4M sodium methoxide in methanol solution (4 mmole). The mixture was stirred for 20 minutes and partitioned between Et2O/ice-H2O/2N HCl (aq.) and the organic phase separated, washed with saturated NaCl solution, and then ice-H2O/saturated NaHCO3 (aq) solution, dried over Na2SO4, filtered, and evaporated. The product was dried in vacuo to give 1.05 g of crude 3-bromo-4'-hydroxybiphenyl which was used without further purification.