Reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].BrC[CH2:22][CH:23]1[CH2:25][CH2:24]1>CN(C)C=O>[CH:23]1([CH2:22][O:12][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=2[O:3][CH:2]([F:13])[F:1])[CH:8]=[O:9])[CH2:25][CH2:24]1Participants
Conditions
- Temperature
- 65 °C
Procedure
To a mixture of 4-difluoromethoxy-3-hydroxy-benzaldehyde (5.0 g, 27 mmol) and potassium carbonate (5.5 g, 40 mmol) in dimethylformamide (30 ml) under inert atmosphere at 60° C. was added bromoethylcyclopropane (5 g, 37 mmol). The mixture was stirred and heated at 65° C. After 1.5 hour, the mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure. The mixture was extracted with ethyl acetate (2×25 ml) and water (25 ml). The organic layer was washed with water (25 ml), brine (25 ml) and dried over magnesium sulfate. The solvent was removed in vacuo to give 3-cyclopropylmethoxy-4-difluoromethoxy-benzaldehyde as an oil (6.4 g, 100%). 1HNMR (CDCl3): δ 0.38–0.44 (m, 2H), 0.62–0.75 (m, 2H), 1.15–1.36 (m, 1H), 3.98 (d, J=4.5 Hz, 2H), 6.78 (t, JH-F=75 Hz, 1H), 7.30–7.50 (m, 3H), 9.96 (s, 1H).
Workup
- temperatureto cool
- filtrationwas filtered
- concentrationThe filtrate was concentrated under reduced pressure
- extractionThe mixture was extracted with ethyl acetate (2×25 ml) and water (25 ml)
- washThe organic layer was washed with water (25 ml), brine (25 ml)
- dry with materialdried over magnesium sulfate
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-534f66fb26db48c4a361a9d6265b6f90
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173058B2
Linked notes
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