Water → 4-(Difluoromethoxy)-3-methoxybenzaldehyde
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:19]([F:25])([F:24])C(OC)=O.O>CN(C=O)C>[F:24][CH:19]([F:25])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-hydroxy-3-methoxybenzaldehyde (6 g), Cs2CO3 (25.7 g) and methyl 2-chloro-2,2-difluoroacetate (5 ml) in DMF (50 ml) was stirred at 90° C. for 1 h. At room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed twice with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1:1 (v/v)] as eluent.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed twice with water, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel in heptane/ethyl acetate [1:1 (v/v)] as eluent
Sources & evidence
- ORD record
- ord-0da08112375748cbbfd6ca233c88a072
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394789B2
Reaction notes
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