Allyl bromide → HCID 69117900, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:15])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C>[CH2:24]([O:15][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH:23]=[CH2:22]

Participants

Procedure

To a solution of 6-chloro-2′-methyl-biphenyl-2-ol (4.75 g, 21.7 mmol) in DMF (30 mL) was added potassium carbonate (4.5 g, 32.6 mmol) and allyl bromide (3.0 mL, 32.6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 4 h. The mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of O to 30% ethyl acetate in hexanes provided 5.6 g (100%) of 2-allyloxy-6-chloro-2′-methylbiphenyl as a light yellow oil.