Potassium Carbonate → HCID 59581715, compound
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:25][C:26]([F:29])([F:28])[F:27])(=O)=O>C(#N)C.CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:25][C:26]([F:29])([F:28])[F:27]Participants
Conditions
- Temperature
- 150 °C
Procedure
To a stirred solution of methyl 4-bromo-3-hydroxybenzoate (2.5 g) in acetonitrile (0.5 mL) and DMF (10 mL) in a microwave tube was added potassium carbonate (2.93 g) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.79 g). The mixture was heated to 150° C. in a microwave oven for 30 minutes. The solvent was removed in vacuum, ethyl acetate was added and the mixture was washed with water. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Recrystallization of the residue from ethanol gave 1.2 g of the title compound. The mother liquor was concentrated in vacuum and purified by aminophase-silica-gel chromatography followed by recrystallized from methanol and water to give further 0.64 g of the title compound.
Workup
- customThe solvent was removed in vacuum, ethyl acetate
- additionwas added
- washthe mixture was washed with water
- washThe organic phase was washed with saturated sodium chloride solution
- dry with materialdried (sodium sulfate)
- customthe solvent was removed in vacuum
- customRecrystallization of the residue from ethanol
Sources & evidence
- ORD record
- ord-8a85e733f8104a4cbdfc6256274c5d44
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388177B2
Reaction notes
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