Benzyl Bromide → 2-(Dimethylamino)-1-(4-fluorophenyl)-2-methyl-3-phenylpropan-1-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH:9]([N:11]([CH3:13])[CH3:12])[CH3:10])=[CH:4][CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(N(C)C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:14])[C:9]([N:11]([CH3:13])[CH3:12])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:10])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
11.2 g of sodium hydride (66%) are washed with hexane to remove oil, and added to 200 ml of dry dimethylacetamide. 50.0 g (0.256 mol) of 1-(4-fluorophenyl)-2-dimethylamino-propan-1-one (prepared by the method described in U.S. Pat. No. 5,534,629) are dissolved in 50 ml of dry dimethylacetamide and added dropwise to the above described solution. Successively, 48.2 g (0.282 mol) of benzyl bromide are slowly added dropwise with stirring and warmed up to 105° C. When the mixture has been stirred at this temperature for 12 h, the reaction mixture is poured to 500 ml of ice/water and extracted with toluene. The organic phase is washed with water, dried over MgSO4 and evaporated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:20) as eluent. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.17 (s,3H), 2.33 (s,6H), 2.96 (d, 1H), 3.39 (d, 1H), 6.87 (m,2H), 7.03-7.13 (m,5H), 8.55 (m, 2H).