3-Methoxypropyne → HCID 22025687, compound

Participants

Reaction Steps

2-Fluoro-4-iodoaniline (2.00 g, 8.44 mmol), CuI (32 mg, 0.17 mmol), and (Ph3P)2PdCl2 (119 mg, 0.17 mmol) were weighed into a flask which was sealed and flushed with N2. A solution of methyl propargyl ether (0.65 g, 9.28 mmol) in TEA (8 mL) was added, then the entire mixture stirred 15 hours at room temperature. The reaction mixture was diluted with diethyl ether (100 mL), filtered through Celite®, then all solvents removed under reduced pressure. The resulting dark brown oil was purified by filtration through a plug of flash silica (10% EtOAc/hexanes as eluant) to afford 2-fluoro-4-(3-methoxy-1-propynyl)aniline as a pale orange oil which rapidly solidified to give a dark orange solid (1.38 g, 91%); 1H NMR [400 MHz, (CD3)2SO] δ 7.07 (dd, J=12.2, 1.8 Hz, 1 H), 6.98 (dd, J=8.2, 1.7 Hz, 1 H), 6.71 (dd, J=9.3, 8.4 Hz, 1 H), 5.56 (s, 2 H), 4.26 (s, 2 H), 3.29 (s, 3 H).

Provenance & Evidence