Methanol → 2-(4-Bromo-phenyl)-5-chloropentanoic acid methyl ester
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][CH2:14][Cl:15])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:16]O>O=S(Cl)Cl>[CH3:16][O:10][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][Cl:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(4-Bromo-phenyl)-5-chloropentanoic acid (3 g, 10.38 mmol) in MeOH (60 mL), SOCl2 (2 mL) was added at 0 degrees Celsius, then the mixture refluxed for 5 h. After cooling, the solution was evaporated to dryness under reduced pressure, then EtOAc was added and the mixture was washed with aq. NaHCO3, the organic layer was dried with MgSO4, and evaporated to give the compound as an oil (2.85 g, 90%). MS: calc'd 304 (MH+), exp 304 (MH+).