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

HRID 454221ノート

反応式

HRID 454221 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10313229titanium(III) trichloride触媒HCID 180Acetone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-97986bb19a6e403b8c830abc576cc4b6
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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