Ammonium Acetate → 4-Fluoro-5-methoxy-2-methyl-1H-indole

HRID 454221노트

반응식

HRID 454221 반응식
[C:1]([CH2:4][C:5]1[C:6]([F:16])=[C:7]([O:14][CH3:15])[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)(=O)[CH3:2].C([O-])(=O)C.[NH4+]>CC(C)=O.[Cl-].[Cl-].[Cl-].[Ti+3]>[F:16][C:6]1[C:7]([O:14][CH3:15])=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[C:1]([CH3:2])[NH:11]2

참가 물질

5

반응물 2

HCID 517165Ammonium AcetateHCID 220307431-(2-Fluoro-3-methoxy-6-nitrophenyl)propan-2-one

생성물 1

HCID 220307284-Fluoro-5-methoxy-2-methyl-1H-indole수율 91%

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 180Acetone용매

실험 절차

To a solution of 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extracted with ether. The organic layer was washed with 0.5N aqueous sodium hydroxide followed by water, brine, dried (MgSO4) and the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with methylene chloride to give 4-fluoro-5-methoxy-2-methylindole (8.15 g, 90%).

후처리

  1. extractionthe mixture was extracted with ether
  2. washThe organic layer was washed with 0.5N aqueous sodium hydroxide
  3. dry with materialdried (MgSO4)
  4. customthe volatiles were removed under vacuum
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride

출처 및 근거

ORD 기록
ord-97986bb19a6e403b8c830abc576cc4b6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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