Dimethylformamide → 4-Bromo-3-fluoro-2-methoxy-5-methylaniline

HRID 17300

反応式

HRID 17300 の反応式
CN(C)C=O.[Br:6]N1C(=O)CCC1=O.[F:14][C:15]1[C:16]([O:23][CH3:24])=[C:17]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[NH2:18]>[Cl-].[Na+].O>[Br:6][C:21]1[C:20]([CH3:22])=[CH:19][C:17]([NH2:18])=[C:16]([O:23][CH3:24])[C:15]=1[F:14]

参加物

5

反応物 3

HCID 6228Dimethylformamide2 回HCID 67184N-bromobutanimideHCID 451220523-Fluoro-2-methoxy-5-methylaniline

生成物 1

HCID 860974514-Bromo-3-fluoro-2-methoxy-5-methylaniline収率 81.6%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

With cooling with ice, an N,N-dimethylformamide (10 ml) solution of N-bromosuccinimide (1.84 g, 10.2 mmol) was dropwise added to an N,N-dimethylformamide (20 ml) solution of 3-fluoro-2-methoxy-5-methylaniline (I-26) (1.55 g, 10.0 mmol), taking 25 minutes, followed by stirring for 18 hours with gradually heating up to room temperature. Saturated brine was added to the reaction liquid, followed by extraction twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure to obtain the entitled compound (1.91 g, 81%) as a brown oily substance.

後処理

  1. temperatureWith cooling with ice
  2. extractionfollowed by extraction twice with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. concentrationthe eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-6573c56e8ad840fab2ca1fc2954a6f24
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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