2-Chloro-4-difluoromethoxy-3-dimethoxymethyl-1-fluorobenzene → 2-Chloro-6-difluoromethoxy-3-fluorobenzaldehyde
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8](OC)[O:9]C)=[C:6]([O:13][CH:14]([F:16])[F:15])[CH:5]=[CH:4][C:3]=1[F:17]>CC(C)=O.O>[Cl:1][C:2]1[C:3]([F:17])=[CH:4][CH:5]=[C:6]([O:13][CH:14]([F:16])[F:15])[C:7]=1[CH:8]=[O:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of crude 2-chloro-4-difluoromethoxy-3-dimethoxymethyl-1-fluorobenzene (181 g, 670 mmol) in acetone (650 mL) and water (150 mL) was added Amberlyst-15 resin (540 g, pre-washed with water) and the mixture was stirred using mechanical stirrer for 40 h at RT. The Amberlyst-15 resin was removed by filtration using celite bed on sintered funnel, and the filtrate was evaporated on a rotary evaporator at RT (Note: aldehyde evaporates at higher temperatures under reduced pressure). The residue was purified by column chromatography on silica gel using ethyl acetate/hexanes (5% to 10%) to obtain the title compound (60 g, 40%).
Workup
- customfor 40 h
- customat RT
- customThe Amberlyst-15 resin was removed by filtration
- customthe filtrate was evaporated on a rotary evaporator at RT
- custom(Note: aldehyde evaporates at higher temperatures under reduced pressure)
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-0e5dd5fc9efe4cd7b3615ab8785f5da5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445510B2
Reaction notes
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