Benzoyl Peroxide → 2-(Benzhydrylideneamino)-4-bromomethylbenzonitrile

HRID 1432857노트

반응식

HRID 1432857 반응식
[C:1](=[N:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1](=[N:14][C:15]1[CH:22]=[C:21]([CH2:23][Br:24])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 179851672-(Benzhydrylideneamino)-4-methylbenzonitrile

생성물 1

HCID 179851902-(Benzhydrylideneamino)-4-bromomethylbenzonitrile

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 2-(benzhydrylidene-amino)-4-methyl-benzonitrile (11.2 g, 37.8 mmol) in 500 mL of CCl4 is added N-bromosuccinimide (7.06 g, 39.7 mmol), and benzoyl peroxide (0.92 g, 3.8 mmol). The solution is heated to reflux for 16 hours. After this time, the solution is filtered and the organic solution is concentrated under vacuum. The residue is purified by column chromatography eluting with a gradient of 20% t-butyl ether/hexanes to 25% t-butyl ether/hexanes. The product is obtained as an oil containing a mixture of the desired monobromide, dibromide and unreacted starting material. The mixture is assayed by proton NMR and is found to have a purity between 60-75%. 1H NMR (CDCl3, 300 MHz) δ7.82 (m, 2H), 7.42 (m, 9H), 6.92 (d, 1H), 6.81 (s, 1H), 4.29 (s, 2H).

후처리

  1. temperatureThe solution is heated
  2. temperatureto reflux for 16 hours
  3. filtrationAfter this time, the solution is filtered
  4. concentrationthe organic solution is concentrated under vacuum
  5. customThe residue is purified by column chromatography
  6. washeluting with a gradient of 20% t-butyl ether/hexanes to 25% t-butyl ether/hexanes
  7. customThe product is obtained as an oil
  8. additioncontaining

출처 및 근거

ORD 기록
ord-04a73c48cbcc4d5da6bcd7ab5f6682cc
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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