[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11].[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1>CN(C)C=O>[CH:14]1([CH2:17][O:13][C:6]2[CH:5]=[C:4]([F:3])[C:9]([CH2:10][OH:11])=[C:8]([F:12])[CH:7]=2)[CH2:16][CH2:15]1Sodium hydride (82 mg, 55%, 1.87 mM) was added to a solution of 3,5-difluoro-4-hydroxymethyl-phenol (300 mg, 1.87 mM) in dimethylformamide (4 mL). After 1 h stirring at room temperature cyclopropylmethylbromide (135 mg, 1.87 mM) was added and stirring continued for 24 h. The mixture was partitioned between water and diethylether. Organic phases were pooled, washed with brine and dried with MgSO4 to yield after evaporation a yellow oil (673 mg). This residue was purified by column chromatography (silica gel; n-hexane/ethylacetate gradient) to yield 287 mg (71%) of the product as a yellowish oil. MS (EI): 214.1 (M)+.
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