Water → 7-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 726612

반응식

HRID 726612 반응식
[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([Br:13])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

생성물 1

HCID 537220087-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran수율 83.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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

후처리

  1. additionUpon completion of addition
  2. extractionThe mixture is then extracted with two 200 mL portions of diethyl ether
  3. washThe combined extracts are washed with two 100 mL portions of an aqueous 10% lithium chloride solution
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d0096e64811a4ecd96ee148cc5e54fe5
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710157

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