HCID 21996962, compound → HCID 70149291, compound
Reaction equation
BrC1C=[CH:6][C:5]([O:8]C(C)C)=[C:4](C(C2C=CC(C)=CC=2)=C)C=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[CH2:30])[CH:23]=1>>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([O:8][CH:5]([CH3:6])[CH3:4])([OH:28])[CH:24]([C:29]([C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[CH2:30])[CH:23]=1Participants
3
Procedure
Employing the same general procedure as for the preparation of 4-bromo-1-isopropoxy-2-[(1-p-tolyl)vinyl]benzene (Compound S), 81.5 mg (0.3 mmol) of 4-bromo-2-[(1-m-tolyl)vinyl]phenol (Compound N) was converted into the title compound using 164 mg (0.6 mmol) of triphenylphosphine, 0.10 mL (108 mg, 0.6 mmol) of diethylazodicarboxylate, 0.05 mL (39 mg, 0.6 mmol) of isopropanol and 3 mL of tetrahydrofuran. The reaction was sluggish necessitating addition (after 23 hours of stirring at ambient temperature) of another equivalent of reagents (initially only ½ of the above amounts were added) and stirring for 4 additional days. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as a pink oil.