tert-Butanol → 1-Bromo-3-tert-butoxy-5-fluorobenzene

Reaction equation

[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:8][C:9]1[CH:10]=[C:11]([Br:16])[CH:12]=[C:13](F)[CH:14]=1>CC(N(C)C)=O>[Br:16][C:11]1[CH:10]=[C:9]([F:8])[CH:14]=[C:13]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1

Participants

Procedure

tert-Butanol (28.2 g) is dissolved in dimethyl acetamide (200 ml). NaH (15.6 g, 60% dispersion in oil) is added over 15 minutes. The reaction mixture is stirred at room temperature for 2 hours. 3,5-difluorobromobenzene (50 g) is added drop wise over 30 minutes. The reaction mixture is stirred at room temperature until shown to be complete by HPLC. The reastion mixture is quenched by addition of water (10 ml), washed with water (1×), dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 7.00 (ddd, 1H), 6.95 (dd, 1H), 6.68 (ddd, 1H), 1.4 (s, 9H).