反应 #361247

反应方程式

sodium bromide

3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one

sulfuric acid

sodium nitrate

→

3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one

收率 49.3%

溶剂

hydrobromic acid

water

chloroform

acetic acid

water

water

反应条件

后处理

1. 1
   温度cooling
2. 2
   workup.STIRRINGthe whole was stirred for 0.5 hour
3. 3
   温度After cooling
4. 4
   过滤The insoluble material was filtered off
5. 5
   其他The organic layer was separated
6. 6
   萃取the aqueous layer was extracted with chloroform
7. 7
   洗涤The combined organic layer was washed with brine
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   workup.ADDITIONtreated with active carbon (0.65 g)
10. 10
    其他The solution was evaporated in vacuo
11. 11
    其他the residue was purified by column chromatography on silica gel with toluene as an eluent

实验过程

To a solution of 3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (9.42 g) in a mixture of acetic acid (1.85 ml), conc. sulfuric acid (9.24 ml) and water (24.56 ml) was added portionwise a solution of sodium nitrate (4.08 g) in water (6.00 ml) with ice salt bath cooling and the whole was stirred for 1 hour. The solution was added to a solution of cuprous bromide (10.02 g) and sodium bromide (9.40 g) in a mixture of 47% hydrobromic acid (27.72 ml) and water (61.52 ml) at 75° C. and the whole was stirred for 0.5 hour. After cooling, ice water (100 ml) and chloroform (200 ml) were added to the mixture. The insoluble material was filtered off. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and treated with active carbon (0.65 g). The solution was evaporated in vacuo and the residue was purified by column chromatography on silica gel with toluene as an eluent to give 3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (6.34 g).

来源