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

HRID 17300

반응식

HRID 17300 반응식
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]

참가 물질

5

반응물 3

HCID 6228Dimethylformamide2회HCID 67184N-bromobutanimideHCID 451220523-Fluoro-2-methoxy-5-methylaniline

생성물 1

HCID 860974514-Bromo-3-fluoro-2-methoxy-5-methylaniline수율 81.6%

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6573c56e8ad840fab2ca1fc2954a6f24
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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