1: magnesium; 1-bromo-4-fluorobenzene With iodine in tetrahydrofuran 2: 5-cyano-isobenzofuran-1-one in tetrahydrofuran; dichloromethane T=-6 - -2°C; 3: With sodium tetrahydroborate; ammonium chloride more than 3 stages;

sodium tetrahydroborate in methanol; toluene T=10 - 15°C; 2 h;

1: With sodium hydroxide; sodium tetrahydroborate in tetrahydrofuran; water T=0 - 15°C; 0.5 h; 2: With phosphoric acid in water 2 h; Heating / reflux;

sodium tetrahydroborate; magnesium in tetrahydrofuran; ethanol; water; ethyl acetate

1: 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile With (1S,2R)-(+)-N-methylephedrine in toluene T=20 - 70°C; 0.75 h; 2: 3-(N,N-dimethylamino)-propylmagnesium chloride in tetrahydrofuran; toluene T=-80°C; 0.2 h; Product distribution / selectivity;

toluene-4-sulfonic acid in toluene T=80 - 85°C; 3 h;