反応 #163496

反応方程式

2,6-Dibromo-4,8-dimethoxy-benzo[1,2-b:4,5-b′]dithiophene

boron tribromide

→

2,6-Dibromo-benzo[1,2-b:4,5-b′]dithiophene-4,8-diol

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他dry/ice acetone bath with an ice/water bath
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   温度to warm to room temperature
4. 4
   workup.STIRRINGwhile stirring for 16 hours
5. 5
   温度before cooling to 0° C
6. 6
   workup.ADDITIONWater (dropwise at first, 150 mL total) and additional dichloromethane (50 mL) were added
7. 7
   その他The dichloromethane was removed on the rotary evaporator
8. 8
   ろ過the solid was collected by filtration
9. 9
   洗浄The solid was washed with water (25 mL) and dichloromethane (25 ml)
10. 10
    その他to give a pale blue/green crude solid
11. 11
    その他to be dried under vacuum
12. 12
    その他used in the next step without additional purification (287 mg)

実験手順

2,6-Dibromo-4,8-dimethoxy-benzo[1,2-b:4,5-b′]dithiophene (500 mg, 1.22 mmol., 1.00 equiv.) and dichloromethane (12 mL) were added to a 50 mL schlenk flask. The mixture was cooled to −78° C. and boron tribromide was added (1.0 M solution in dichloromethane, 2.5 mL, 2.5 mmol., 2.1 equiv.) slowly. The mixture was stirred for 15 minutes at −78° C. before replacing the dry/ice acetone bath with an ice/water bath. The reaction mixture was left to warm to room temperature while stirring for 16 hours before cooling to 0° C. Water (dropwise at first, 150 mL total) and additional dichloromethane (50 mL) were added. The dichloromethane was removed on the rotary evaporator and the solid was collected by filtration. The solid was washed with water (25 mL) and dichloromethane (25 ml) to give a pale blue/green crude solid to be dried under vacuum and used in the next step without additional purification (287 mg). 1H NMR (400 MHz, CDCl3) δ 10.13 (s, 2H), 7.71 (s, 2H).

出典