Allyl Alcohol → 1-Allyloxy-3-bromo-5-fluorobenzene

Reaction equation

[CH2:1]([OH:4])[CH:2]=[CH2:3].[H-].[Na+].[F:7][C:8]1[CH:9]=[C:10]([Br:15])[CH:11]=[C:12](F)[CH:13]=1>CC(N(C)C)=O>[CH2:1]([O:4][C:12]1[CH:13]=[C:8]([F:7])[CH:9]=[C:10]([Br:15])[CH:11]=1)[CH:2]=[CH2:3]

Participants

Procedure

To a DMA (400 ml) solution of allyl alcohol (8.9 g, 0.154 mol), at room temperature (r.t.) is added NaH (60% oil dispersion) (6.4 g, 0.160 mol) in portions. The mixture is stirred at r.t. for 1.5 h followed by the slow addition of 3,5-difluoro bromobenzene (17.9 ml, 30 g, 0.155 mol). The reaction mixture is stirred at r.t. overnight. The reaction is quenched by the addition of 1500 ml of water and extracted with ether (4×300 ml). The organic layer is dried over MgSO4 and concentrated at reduced pressure to yield 24.6 g (69%) of a colorless oil after flash chromatography (pentane, rf.=0.3). Anal. Calc. for C9H8BrFO: C, 46.78; H, 3.49. Found: C. 46.18, H, 3.45. Calculated mass for C9H8OFBr: 229.97. Mass found for C9H8OFBr: (OAMS) ES−: 189.0 (M-allyl)