Hydrochloric Acid → Methyl 4-bromo-2,6-difluorobenzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.S(Cl)(Cl)=O.[CH3:17]N(C=O)C.Cl>C(Cl)Cl.CO>[CH3:17][O:7][C:6](=[O:8])[C:5]1[C:4]([F:12])=[CH:3][C:2]([Br:1])=[CH:10][C:9]=1[F:11]Participants
7
Procedure
To a suspension of 4-Bromo-2,6-difluoro-benzoic acid (5 g, 21 mmol) in DCM (10 mL) is added thionyl chloride (15 mL) and DMF (0.5 mL). The mixture is stirred at room temperature for 2.5 h. It is then cooled to 0° C. and MeOH (20 mL) is added carefully causing vigorous HCl evolution. After stirring for an additional 0.5 h, the clear solution is partitioned between DCM (50 mL) and water (50 mL). The organic layer is washed with saturated NaHCO3, brine, dried over MgSO4 and the solvent is removed under vacuum to afford the title compound as a pale yellow oil which is used without further purification.
Workup
- temperatureIt is then cooled to 0° C.
- stirringAfter stirring for an additional 0.5 h
- customthe clear solution is partitioned between DCM (50 mL) and water (50 mL)
- washThe organic layer is washed with saturated NaHCO3, brine
- dry with materialdried over MgSO4
- customthe solvent is removed under vacuum
Sources & evidence
- ORD record
- ord-506672a75a344ea8a878c8e3cd92f0b0
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893058B2
Reaction notes
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