Potassium Carbonate → HCID 58046301, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:30]=[C:29](F)[CH:28]=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:29]2[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([F:19])[CH:30]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 4-chloro-3-(trifluoromethyl)phenol (1.05 g, 5.34 mmol) in DMSO (10 mL) was added potassium carbonate (2.20 g 13.4 mmol, 2.5 eq.) and the suspension was left to stir for 5 minutes after which, ethyl 2,4-difluorobenzoate (1.0 g, 5.34 mmol) was added and the reaction mixture left to stir at 110° C. under nitrogen for 16 hours. The reaction mixture was cooled to room temperature and quenched with 1N NaOH (10 mL) then extracted into ethyl acetate (2×30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered and evaporated. The resulting residue was purified by column chromatography (SiO2, 1:1 ethyl acetate: heptane) to give the desired product (mixture of regioisomers) as a colourless oil (1.8 g, 93% yield). This was taken directly on to the next step.
Workup
- waitthe suspension was left
- additionwas added
- waitthe reaction mixture left
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with 1N NaOH (10 mL)
- extractionthen extracted into ethyl acetate (2×30 mL)
- washThe combined organic layers were washed with brine (30 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe resulting residue was purified by column chromatography (SiO2, 1:1 ethyl acetate: heptane)
Sources & evidence
- ORD record
- ord-04caedc2bb754d629864d6a4a9a9f568
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685977B2
Reaction notes
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