[Br-].[CH:2]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC(C)([O-])C.[K+].[N+:33]([C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH:38]=O)([O-:35])=[O:34]>C1COCC1>[C:2]1(=[CH:38][C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[N+:33]([O-:35])=[O:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1To a slurry of cyclohexyl triphenylphosphonium bromide (16.6 g) in THF (100 mL) at 24° C. was added potassium t-butoxide (4.38 g). The mixture was stirred for 30 min. o-Nitrobenzaldehyde (3.93 g) in THF (50 mL) was added dropwise below 30° C. and stirred for 30 min. The mixture was then partitioned between EtOAc and ice water. The EtOAc layer was washed well with water, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel with 5% EtOAc/hexanes to give 1-(cyclohexylidenemethyl)-2-nitrobenzene.
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