Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].Cl[CH2:15][O:16][CH3:17].Cl.[CH3:19]N(C)C=O>>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[O:11][CH2:15][O:16][CH3:17]Participants
6
Procedure
To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in N,N-dimethylformamide (5 mL) were added sodium hydride (60% 1.0 g) and (chloromethyl)methyl ether (2.1 g) at room temperature, and this mixture was stirred for 48 hours at the same temperature. This reaction mixture was poured into 2 mol/L hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.22 g).
Workup
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-634103d164394d749f715694d9554186
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829040B2
Linked notes
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