Bromide ion → 3-Bromo-1h-indole

HRID 278396노트

반응식

HRID 278396 반응식
[Br-:1].COC1C=CC(C(O)C2C=CC(OC)=CC=2)=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1.C[N:32]1[CH2:36]CCC1=O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:30]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:32][CH:36]=1

참가 물질

7

반응물 4

HCID 259Bromide ionHCID 6101p-Toluenesulfonic acidHCID 13387N-methyl-2-pyrrolidoneHCID 69768p,p'-Dimethoxybenzhydryl alcohol

생성물 1

HCID 27632773-Bromo-1h-indole수율 87%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the above bromide (1.09 g, 2.8 mmol) in benzene (60 mL) and N-methylpyrrolidinone (6 mL) was added 4,4′-dimethoxybenzhydrol (818 mg, 3.4 mmol) and p-toluenesulfonic acid (532 mg, 2.8 mmol), and the mixture was heated to reflux. After 24 hours the reaction was cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed with NaHCO3 (2×), H2O (2×), and brine(2×). The organic layer was dried over anhydrous MgSO4, filtered and solvent was removed in vacuo. The crude material was purified via column chromatography (10% EtOAc-hexane) to provide the desired DMB protected 3-bromo indole derivative (1.5 g, 2.4 mmol, 87% yield) as an orange solid: (MS m/z (M+H) 615, 617).

후처리

  1. temperaturethe mixture was heated to reflux
  2. washThe organic layer was washed with NaHCO3 (2×), H2O (2×), and brine(2×)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customsolvent was removed in vacuo
  6. customThe crude material was purified via column chromatography (10% EtOAc-hexane)
  7. customto provide the desired DMB

출처 및 근거

ORD 기록
ord-9bd2e99fc12a412c8570c5e815271937
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359130B1

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