[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9]O.CC(C)(O)[C:13]#[N:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1.CCCCCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:13]#[N:14]To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in Benzene (0.064M) at room temperature was added acetone cyanohydrin (1.5 eq), 1-1′(Azodicarbonyl)dipiperidine (1.5 eq) then dropwise over 5 min triphenyl phosphine (1.5 eq). The mixture was stirred at room temperature for 12 h, diluted with hexane (0.03M) and filtered on pad of silica gel. Fractions containing the desired material were combined and concentrated. A second purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 30%, in 30 min) afforded the desired compound as a colorless oil.
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