N-bromobutanimide → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 629317

반응식

HRID 629317 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Br:13]N1C(=O)CCC1=O>FC(C1C=CC=CC=1)(F)F.C(OCC)(=O)C.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][Br:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 316201Methyl 5-bromo-2-methylbenzoate

생성물 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoate수율 69%

시약·촉매·용매 3

HCID 6547Azobisisobutyronitrile촉매HCID 7368(Trifluoromethyl)benzene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

To a solution of methyl 5-bromo-2-methylbenzoate (5.27 g) in trifluoromethylbenzene (50.0 mL) were added AIBN (0.04 g) and N-bromosuccinimide (4.50 g), and the mixture was stirred at 90° C. for 4 hr under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.89 g).

후처리

  1. washthe mixture was washed with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a7919ee28acd4adba6209dc2b2df2be1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315458B2

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