Methanol → Methyl 4-bromo-2-phenylbutanoate

Reaction equation

[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:18]O>>[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([O:7][CH3:18])=[O:6]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 167406054-Bromo-2-phenylbutanoic acid

Product 1

HCID 19050128Methyl 4-bromo-2-phenylbutanoate

Procedure

The product of Example 4 (22 g) in methanol (100 ml) was treated dropwise with SOCl2 (7.3 ml, 0.1M) at about 5° C. The reaction mixture was allowed to warm to room temperature. The solvent was evaporated off and the residue partitioned between water and IPE. The organic phase was dried and evaporated to give the title compound as an oil (23 g). Bp. 85°/0.1 mm.