[H-].[Na+].[CH2:3]([OH:8])[CH:4]=[CH:5][CH2:6][OH:7].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH3:18])[CH:12]=1>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:7][CH2:6][CH:5]=[CH:4][CH2:3][OH:8])=[CH:12][C:13]=1[CH3:18]To a suspension of NaH (1.0 g, 60% oil dispersion) in 80 mL THF was slowly added but-2-ene-1,4-diol (2.0 g, 22 mmol) as a solution in 5 mL THF at room temperature. To this mixture was added dropwise 4-bromomethyl-1-fluoro-2-methyl-benzene (5.0 g, 24 mmol) and the resulting stirred for 8 h at room temperature. The reaction was quenched by the slow addition of 50 mL of saturated NH4Cl and the mixture extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (2×60 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 2.3 g of the title compound as a light yellow oil.
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