反应详情

A 100 mL of reactor equipped with magnetic stir bar was charged with 140 mg (0.15 mmol) of {[(t-Bu)2P(OH)]2PdCl}2 (from Experiment 7), 2.03 g (10.0 mmol) of 4-bromothioanisole, 1.83 g (15.0 mmol) of PhB(OH)2 and 4.16 g (30.0 mmol) of K2CO3 in 13 mL of DME and 7 mL of H2O. The reaction mixture was refluxed for 12 h until the starting material was completely consumed as judged by TLC. The reaction was cooled to room temperature, transferred to a separatory funnel, and diluted with 300 mL of hexane and 100 mL of H2O. The layers were separated, and organic layer was washed with H2O (2×100 mL), brine (100 mL), and dried over mgSO4, filtered, and solvents removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silicon gel using hexane as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to give 1.90 g (95% yield) of 4-phenylthioanisole. It was >95% pure by 1H NMR and GC/MS. 1H NMR (300 MHz, CDCl3): δ7.47-7.39 (m, 5H), 7.31 (m, 2H), 7.22 (m, 2H), 2.39 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ140.5, 138.0, 137.6, 128.8, 127.4, 127.1, 126.9, 126.8 ppm.

1. customA 100 mL of reactor equipped with magnetic stir bar
2. temperatureThe reaction mixture was refluxed for 12 h until the starting material
3. customwas completely consumed
4. customtransferred to a separatory funnel
5. additiondiluted with 300 mL of hexane and 100 mL of H2O
6. customThe layers were separated
7. washorganic layer was washed with H2O (2×100 mL), brine (100 mL)
8. customdried over mgSO4
9. filtrationfiltered
10. customsolvents removed from the filtrate by rotary evaporation
11. customThe resulting residue was chromatographed on silicon gel
12. concentrationThe eluate was concentrated by rotary evaporation