Chloroform → 4-(2-Nitrophenyl)morpholine

Participants

Reaction Steps

According to General Procedure B, a mixture of 2-nitro chlorobenzene (79 mg, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol) and 12f (0.4 mL of 0.05 M solution in PhMe) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (40% Et2O in hexane, silica gel) gave 52d (45 mg, 43%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.79 (d, 1H, J=8.1 Hz), 7.52-7.47 (m, 1H), 7.15 (d, 1H, J=8.3 Hz), 7.10-7.06 (m, 1H), 3.85-3.83 (m, 4H), 3.07-3.04 (m, 4H); 13C NMR (75.5 MHz, CDCl3) δ 145.8, 143.7, 133.5, 125.9, 122.3, 120.9, 66.8, 52.1.

Provenance & Evidence