Methanol → Methyl 2-bromo-3-fluorobenzoate
Reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:16]O>>[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]Participants
4
Procedure
To a suspension of 2-bromo-3-fluorobenzoic acid (300 mg, 1.37 mmol) in methanol (10 mL) at rt, was added SOCl2 (0.11 mL, 1.51 mmol) and the mixture was stirred at rt for 18 h. The solvent was distilled off under reduced pressure. The crude was basified by adding saturated aqueous NaHCO3 solution and the aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The obtained crude product was used in the next step without further purification.
Workup
- distillationThe solvent was distilled off under reduced pressure
- additionby adding saturated aqueous NaHCO3 solution
- extractionthe aqueous layer was extracted with EtOAc (3×25 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe obtained crude product
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-d450ec277c2f4bbda5251542be6a89b7
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260434B2
Reaction notes
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