3-Bromothiophene → HCID 66351280, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromothiophene (7.20 g, 44.16 mmol), dodecylamine (12.28 g, 166.24 mmol), Cu (0.14 g, 2.21 mmol), CuI (0.42 g, 2.21 mmol), K3PO4 (18.75 g, 88.32 mmol), and N,N-dimethylethanolamine (60 mL) is purged with N2. The reaction mixture is then stirred for 2 days at 90° C. under nitrogen. The reaction mixture is quenched with water and extracted with diethyl ether followed by washing with brine. The organic layer is dried over Na2SO4. The crude compound is purified by column chromatography on silica gel with 0-5% ethyl acetate in hexane as eluent to give 3-dodecylaminothiophene (6a) as a brown solid (5.75 g, 49%). 1H-NMR (400 MHz) ppm 7.11 (dd, 1H, J=3.0 Hz, J=5.2 Hz), 6.58 (dd, 1H, J=1.5 Hz, J=5.1 Hz), 5.88 (dd, 1H, J=1.5 Hz, J=3.0 Hz), 3.02 (t, 2H, J=7.1 Hz), 1.58 (m, 2H), 1.35 (m, 18H), 0.86 (t, 3H, J=6.8 Hz).

Provenance & Evidence