N-bromobutanimide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

HRID 2061737노트

반응식

HRID 2061737 반응식
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

생성물 1

HCID 106781242-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene수율 44%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 2-methyl-1-nitro-3-trifluoromethyl-benzene (5.0 g, 24.4 mmol) in CCl4 (300 mL) was added N-bromosuccinimide (4.35 g, 24.4 mmol) and benzoyl peroxide (0.11 g, 0.45 mmol). The mixture was heated to reflux and exposed to light (300 W) for 20 h. The mixture was cooled to room temperature, filtered and concentrated. Purification by column chromatography (EtOAc-hexanes) afforded 3.03 g (44%) of the benzyl bromide, a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.93 (s, 2 H), 7.63 (t, J=8.1 Hz, 1 H), 7.94 (d, J=7.8 Hz, 1 H), 8.06 (d, J=8.1 Hz, 1 H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-4ef07aa3f6014001aeeb6c161aacc574
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283373B2

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