N-(2-cyanophenyl)-2,2,2-trifluoroacetamide

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

Procedure: N-(2-Cyanophenyl)-2,2,2-trifluoroacetamide (3 g, 0.014 mol) was added to sodium hydride (60% in oil, 0.62 g, 0.026 mol) in THF (40 ml) under nitrogen and stirred for 4 h. Methyl iodide (8.7 ml, 0.14 mol) was added and stirring continued overnight. The mixture was poured onto brine and extracted with ethyl acetate, dried over sodium sulphate and evaporated to give the product (3 g), MS (+EI) 228 (M+). 1H NMR (CDCl3) 7.8 (1H, d), 7.7 (1H, dd), 7.4 (1H, dd), 7.4 (1H, d), 3.43 (3H, s). stirring continued overnight The mixture was poured onto brine extracted with ethyl acetate dried over sodium sulphate evaporated

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

Procedure: Follow the procedure of Example 3 (Steps B3–B5) but start with N-(2-cyano-phenyl)-2,2,2-trifluoroacetamide (synthesis described in J. Fluorine Chem. 1981, 18, (2), 185–95) and tert-butyl bromoacetate to obtain the title compound: MS 310(M+H), TLC (silica gel, dichloromethane/methanol, 7:1) Rf=0.38.