[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1.[OH-].[Na+].O>C(Cl)Cl>[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH:7][C:6]2[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:4]([O:3][CH3:2])[CH:5]=2)=[CH:35][CH:34]=1To a solution of (3,5-dimethoxybenzyl)triphenylphosphonium bromide (300 mg, 0.6 mM), 4-fluorobenzaldehyde (133 mg, 1.07 mM), catalytic amounts of 18 crown-6 in DCM was added 1.5 mL of 50% solution of NaOH. The reaction was stirred for 5 h and water was added. The water phase was extracted with ethyl acetate and the organic phase was combined. The crude product was purified through flash chromatography eluting with hexanes/ethyl acetate (98:2).
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