N-Bromosuccinamide → 4-Bromo-2-butyl-5-methoxy-1-indanone

HRID 7845

반응식

HRID 7845 반응식
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[Br:17]NC(=O)CCC(N)=O>CN(C)C=O.CCOC(C)=O>[Br:17][C:11]1[C:10]([O:14][CH3:15])=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]2=[O:16]

참가 물질

5

반응물 2

HCID 9834204N-BromosuccinamideHCID 120457522-Butyl-5-methoxy-1-indanone

생성물 1

HCID 219909024-Bromo-2-butyl-5-methoxy-1-indanone

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-butyl-5-methoxy-1-indanone (1.869 g, 8.56 mmol) in anhydrous dimethylformamide (8.6 mL) was treated with N-bromosuccinamide (1.676 g, 9.42 mmol). The resulting mixture was stirred under a nitrogen atmosphere and at room temperature for 14 hours, and then heated in an oil bath at 50° C. for 4 hours. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL), washed with water (4×50 mL) and brine (50 mL), dried over MgSO4, and evaporated under vacuum to a dark amber oil (2.468 g). The crude product was purified by column chromatography on EM silica gel 60 (230-400 mesh, 620 mL dry, packed under CH2Cl2), using CH2Cl2 as eluting solvent, to afford 4-bromo-2-butyl-5-methoxy-1-indanone (1.267 g, contains approx. 3% of the 6-bromo isomer) as a pale tan solid. Earlier fractions afforded the 6-bromo isomer.

후처리

  1. temperatureheated in an oil bath at 50° C. for 4 hours
  2. temperatureAfter cooling to room temperature
  3. washwashed with water (4×50 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum to a dark amber oil (2.468 g)
  6. customThe crude product was purified by column chromatography on EM silica gel 60 (230-400 mesh, 620 mL dry, packed under CH2Cl2)
  7. washas eluting solvent

출처 및 근거

ORD 기록
ord-ea29327def8e4fbe9589fa709757dc0d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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