تفاعل #80932

معادلة التفاعل

water

7-amino-2,3-dihydro-2,2-dimethylbenzofuran

N-bromosuccinimide

→

7-amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

المردود 83.3%

المذيبات

N,N-dimethylformamide

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   استخلاصThe mixture was then extracted with two 200 mL portions of diethyl ether
3. 3
   غسيلThe combined extracts were washed with two 100 mL portions of an aqueous 10% lithium chloride solution
4. 4
   تجفيفThe organic layer was dried with magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزThe filtrate was concentrated under reduced pressure

الإجراء التجريبي

A stirred solution of 10.0 grams (0.061 mole) of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran in 150 mL of N,N-dimethylformamide was cooled in an ice-water bath, and a solution of 10.9 grams (0.061 mole) of N-bromosuccinimide in 50 mL of N,N-dimethylformamide was added in one portion. Upon completion of addition, the reaction mixture was maintained in the ice-water bath for about one hour. After this time the reaction mixture was poured into about 600 mL of water. The mixture was then extracted with two 200 mL portions of diethyl ether. The combined extracts were washed with two 100 mL portions of an aqueous 10% lithium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 12.3 grams of 7-amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure.

المصدر