反应 #65906

反应方程式

1,3-di-t-butylbenzene

bromine

→

title compound

收率 99.9%

2,4-bis(1,1-dimethylethyl)-1-bromobenzene

收率 99.9%

溶剂

acetic acid

反应条件

后处理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGthe reaction mixture was stirred for a further 45 minutes
3. 3
   温度After cooling
4. 4
   过滤the precipitated silver bromide was filtered off
5. 5
   洗涤washed with acetic acid
6. 6
   其他The combined filtrates were partitioned between dichloromethane and water
7. 7
   萃取the aqueous layer was further extracted with dichloromethane
8. 8
   洗涤The combined organic extracts were washed with aqueous sodium bisulfite
9. 9
   干燥dried over sodium sulfate
10. 10
    过滤filtered
11. 11
    其他evaporated
12. 12
    其他Acetic acid was then removed by azeotropic distillation with heptane
13. 13
    workup.DISTILLATIONDistillation of the residue under reduced pressure

实验过程

To a solution of 5.00 g (26.3 mmoles) of 1,3-di-t-butylbenzene in 15 ml of acetic acid was added 4.47 g (26.3 mmoles) of silver nitrate. The mixture was stirred in an oil bath at 75°-80° and then bromine (4.21 g, 26.3 mmoles) was added in small portions over 2 hours. After the addition was complete, the reaction mixture was stirred for a further 45 minutes. After cooling, the precipitated silver bromide was filtered off and washed with acetic acid. The combined filtrates were partitioned between dichloromethane and water and the aqueous layer was further extracted with dichloromethane. The combined organic extracts were washed with aqueous sodium bisulfite, dried over sodium sulfate, filtered, and evaporated. Acetic acid was then removed by azeotropic distillation with heptane. Distillation of the residue under reduced pressure gave 7.07 g of the title compound, b.p. 82°-84° C. (1 mm). The structural assignment was supported by 1H NMR and 13C NMR.

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