N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3-nitrobenzene

HRID 901856

반응식

HRID 901856 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][Br:12]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 1235372-Bromo-6-nitrotoluene

생성물 1

HCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzene수율 80%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 1-bromo-2-methyl-3-nitro-benzene (16.095 g, 74.5 mmol), 1-Bromo-pyrrolidine-2,5-dione (13.26 g, 74.5 mmol), benzoyl peroxide (180 mg, 0.74 mmol) in CCl4(100 ml) was heated under reflux overnight. After removing the solvent by using rotary evaporator, the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 1-bromo-2-bromomethyl-3-nitro-benzene as a yellow solid (17.55 g, 80%). 1H NMR (CDCl3, 300 MHz) δ: 4.89(s, 2H), 7.35(dd, 1H, J1=J2=8.1 Hz), 7.88(dd, 2H, J1=1.6 Hz, J2=8.1 Hz).

후처리

  1. temperatureunder reflux overnight
  2. customAfter removing the solvent
  3. customevaporator
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting brown residue
  9. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-12e466c0019e4b88a45063cd753063bf
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365063B2

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