[CH2:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[OH:10])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[C:19](F)=[CH:20][C:21]([F:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24]>CS(C)=O>[F:27][C:21]1[CH:20]=[C:19]([O:10][C:4]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=2[CH2:1][CH3:2])[C:18]([Cl:17])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]To a solution of 2-ethyl-4-fluorophenol (364 mg, 2.60 mmol) in DMSO (10 mL) was added cesium carbonate (1690 mg, 5.19 mmol) and the mixture stirred at room temperature for 5 minutes. 5-chloro-2,4-difluorobenzoic acid (500 mg, 2.6 mmol) was added and the reaction heated to 110° C. for 18 hours. The reaction was cooled and quenched by the addition of 1N HCl (30 mL) and extracted into ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (30 mL) and concentrated in vacuo before purifying using silica gel column chromatography eluting with ethylacetate:heptane 12:88 to 100:0 to furnish the title compound as a white solid (465 mg, 57%).
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