Potassium Carbonate → HCID 70558916, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.Cl[C:13]([F:19])([F:18])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:18][CH:13]([F:19])[O:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]Participants
6
Conditions
- Temperature
- 120 °C
Procedure
5-Bromo-2-nitrophenol (1 g, 4.59 mmol) and methyl 2-chloro-2,2-difluoroacetate (991 mg, 6.9 mmol) were dissolved in dry DMF (3 mL). Potassium carbonate (1.27 g, 9.18 mmol) was added and the reaction was stirred at 120° C. for 1 hour. The reaction was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 20% dichloromethane in hexanes to afford the title compound as a dark brown oil (375 mg, 30%).
Workup
- temperatureThe reaction was cooled to room temperature
- washThe organic solution was washed with water (20 mL), brine (20 mL)
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
- washeluting with 20% dichloromethane in hexanes
Sources & evidence
- ORD record
- ord-100a5e7dafbe4ee7b03bbbf342388ce7
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409907B2
Reaction notes
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