1-fluoro-4-(1-isothiocyanatoethyl)benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the crude N-ethyl glycine (18.4 g), 1-(4-fluorophenyl)-ethyl-isothiocyanate (18.1 g), triethyl amine (20.2 g) and chloroform (300 mL) was heated at reflux for 18 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 1N HCl (2×300 mL), then evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (8.8 g) as a light yellow solid, m.p. 93°-95° C. Anal. Calcd. for. C13H15F N2O S: C, 58.63; H, 5.68; N, 10.52. Found: C, 58.69; H, 5.64; N, 10.58. Mass spectrum (EI, M.+) m/z 266. was heated at reflux for 18 hours The solvent was evaporated The residue was dissolved in ethyl acetate (400 mL) The organic phase was washed with 1N HCl (2×300 mL) evaporated to dryness Crystallization from ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-(4-benzyl-isoxazol-3-yl)-phenylamine and 4-fluoro-α-methyl-benzyl isothiocyanate in dimethylformamide (5 mL) is stirred for 12 hours at room temperature. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.4 g crude product as a yellow solid. The latter is recrystallized from ethyl acetate/hexane to give 0.9 g product as a yellow solid. MS: m/z 433 (M+H)+. The reaction mixture is then partitioned between ethyl acetate and water The organic layer is washed with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure to give 1.4 g crude product as a yellow solid The latter is recrystallized from ethyl acetate/hexane