Ammonium Chloride → 3-(4-Bromobutyl)-4'-hexyl-2,2'-bithiophene

Participants

Reaction Conditions

Reaction Steps

A mixture of a saturated solution of NaHCO3 (115 ml) and DME (230 ml) was sparged with argon for 45 minutes. 2-bromo-3-(4-bromobutyl)thiophene (10.4 g, 35 mmol) and 2-(4-hexylthiophen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (9.9 g, 35 mmol) were added, followed by addition of Pd(PPh3)4. After warming up to 80° C., the mixture became first bright yellow, and then dark orange. After stirring at 80° C. for 18 h, a saturated solution of NH4Cl (aq, 210 ml) was added, and the mixture was extracted with ether. The organic phase was washed with water, a saturated solution of NaHCO3 and brine. After drying over magnesium sulfate and solvent removal, the dark orange oil was purified by column chromatography using hexanes as the eluent. The product (6.07 g, 45% yield) was isolated as a pale yellow oil and used without further purification. 1H-NMR (ppm, CDCl3): 0.87 (3H, t, J=6.96 Hz), 1.25-1.36 (6H, m), 1.61 (2H, m), 1.76 (2H, m), 1.88 (2H, m), 2.58 (2H, t, J=8.52 Hz), 2.76 (2H, t, J=7.56 Hz), 3.38 (2H, t, J=6.72 Hz), 6.86-6.93 (3H, m), 7.14 (1H, d, J=5.2 Hz); 13C-NMR (ppm, CDCl3): 14.1, 21.2, 22.3, 29.0, 29.2, 30.5, 30.7, 31.0, 31.1, 31.8, 121.2, 123.6, 128.1, 129.8, 132.0, 135.5, 137.1; ESI-MS (m/z) found: 385.06, [M+H], calculated: 385.06.

Provenance & Evidence