反应详情

温度

68 °C

To a suspension of magnesium (1.14 g, 46.9 mmol) in dry THF (50 mL) is added iodine (100 mg) followed by slow addition of 6-bromobenzo[b]thiophene (5.00 g, 23.5 mmol) in dry THF (100 mL) at 64° C. (internal temperature) under a nitrogen atmosphere. During the addition, dry toluene (20 mL) is added to the mixture. When addition is completed, the mixture is heated at 68° C. (internal temperature) for 3 hours then cooled to −60° C. where a stream of sulfur dioxide is passed through the solution for 10 minutes. The mixture is allowed to warm to room temperature, the sulfur dioxide bubbling continues for an additional 5 minutes, and the mixture is stirred for 45 minutes. After filtration and concentration, a reddish solid is obtained (8.0 g), which is diluted with dichloromethane (235 mL), treated with N-chlorosuccinimide (3.45 g, 25.8 mmol) at room temperature, and stirred for 2 hours. After filtration and concentration, a reddish solid is obtained (5.8 g), which is diluted with dichloromethane (234 mL), treated with aminodiphenylmethane (20.2 mL, 117 mmol) at 0° C. and the mixture is stirred for 1 hour. Water (200 mL) is added and the mixture is extracted with dichloromethane (3×200 mL). The organic layers are dried (MgSO4) and concentrated. The crude product is suspended in dichloromethane/hexane before it is filtered to give the title compound as a white solid. The filtrate is concentrated and the residue is chromatographed on silica gel (dichloromethane) to give a second crop of title compound (total 2.52 g). ES+(m/z) 378 [M−H].

1. additionis added to the mixture
2. additionWhen addition
3. temperatureto warm to room temperature
4. filtrationAfter filtration and concentration
5. customa reddish solid is obtained (8.0 g), which
6. stirringstirred for 2 hours
7. filtrationAfter filtration and concentration
8. customa reddish solid is obtained (5.8 g), which
9. stirringthe mixture is stirred for 1 hour
10. extractionthe mixture is extracted with dichloromethane (3×200 mL)
11. dry with materialThe organic layers are dried (MgSO4)
12. concentrationconcentrated
13. filtrationis filtered