Water → Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[F:17][CH:13]([F:18])[O:11][C:4]1[CH:3]=[C:2]([F:1])[C:7]([CH2:8][OH:9])=[C:6]([F:10])[CH:5]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
500 mg 3,5-difluoro-4-(hydroxymethyl)phenol (3.12 mmol, 1.0 eq.) were dissolved in DMF. 523 mg sodium chloro(difluoro)acetate (3.44 mmol, 1.1 eq.), 1.22 g cesium carbonate (3.75 mmo, 1.2 eq) and 0.20 mL water (10.9 mmol, 3.5 eq.) were added. The reaction mixture was stirred at 100° C. over night. The reaction mixture was divided between water and ethyl acetate. The aqueous layer was washed twice with ethyl acetate. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo. The crude product was purified by flash chromatography to provide 161 mg (0.69 mmol, 22%) of the 56% pure target compound.
Workup
- washThe aqueous layer was washed twice with ethyl acetate
- washThe combined organic layers were washed with brine
- customdried over a silicon
- filtrationfilter
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-ccdc2f7392d948c583bacedff73d2af3
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422268B2
Reaction notes
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