Methanol → Methyl 4-(allyloxy)-5-bromo-2-chlorobenzoate
Reaction equation
[CH2:1]([O:4][C:5]1[C:13]([Br:14])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([Cl:15])[CH:6]=1)[CH:2]=[CH2:3].O=S(Cl)Cl.[CH3:20]O>>[CH2:1]([O:4][C:5]1[C:13]([Br:14])=[CH:12][C:8]([C:9]([O:11][CH3:20])=[O:10])=[C:7]([Cl:15])[CH:6]=1)[CH:2]=[CH2:3]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of compound 21 (17.0 g, 58.0 mmol) in MeOH (380 mL) was added dropwise SOCl2 (21.1 mL, 291 mmol) at 0° C. under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 30 min and then, stirred at 0° C. for 14 hours. The mixture was concentrated in vacuo and poured into aq. saturated NaHCO3 solution and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the crude product 39 (17.7 g, 99%) as a white solid.