(2-chloro-4-formylphenyl) trifluoromethanesulfonate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trifluoro-methanesulfonic acid 2-chloro-4-formyl-phenyl ester (I-6a: 10.0 g), 3-cyano-phenyl-boronic acid (5.26 g) and palladium tetrakis(triphenylphosphine) (3.00 g) were combined in 100 mL of dimethoxyethane, then treated with 10 mL of a 2M aqueous sodium carbonate solution before being heated in a 100° C. oil bath. After 24 hours, the reaction mixture was cooled to ambient temperature, the organic phase was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in heptane to afford the title compound (I-6b). the reaction mixture was cooled to ambient temperature the organic phase was separated dried over magnesium sulfate filtered concentrated under reduced pressure The resulting residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in heptane

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

Procedure: The title compound was prepared by reacting trifluoro-methanesulfonic acid 2-chloro-4-formyl-phenyl ester (5 g, 17.4 mmol) with 4-methoxyphenylboronic acid (3.44 g, 22.6 mmol) according to Method B to yield 3.83 g (89%) of white solid: mp 85-87° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.07 (2H, d, J=8.83 Hz), 7.46 (2H, d, J=8.45 Hz), 7.63 (1H, d, J=7.87 Hz), 7.92 (1H, dd, J=7.87 Hz, J=1.56 Hz), 8.07 (1H, d, J=1.49 Hz); 13C NMR (DMSO-d6): δ 55.14, 113.72, 127.80, 129.72, 130.42, 130.82, 132.15, 132.21, 136.11, 144.90, 159.33, 191.73; IR 1692 cm−1; MS (EI) m/z 246/248 M+.