Benzoyl Peroxide → 3-(Bromomethyl)-4-[(diphenylmethylidene)amino]-2-(trifluoromethyl)benzonitrile

HRID 913560ノート

反応式

HRID 913560 の反応式
[C:1]1([C:7](=[N:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[C:16]=2[CH3:27])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:35])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:35][CH2:27][C:16]1[C:17]([C:23]([F:24])([F:25])[F:26])=[C:18]([CH:21]=[CH:22][C:15]=1[N:14]=[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:19]#[N:20]

参加物

6

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 866206794-[(Diphenylmethylidene)amino]-3-methyl-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 866206803-(Bromomethyl)-4-[(diphenylmethylidene)amino]-2-(trifluoromethyl)benzonitrile収率 95%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of the benzonitrile (3.53 g, 9.69 mmol) from step D in CCl4 (90 mL) was added NBS (1.98 g, 11.14 mmol) and benzoyl peroxide (70%, 0.352 g, 1.45 mmol). The mixture was heated at reflux for 3 h. After cooling to ambient temperature, the reaction was diluted with CH2Cl2 (100 mL), washed with 1N NaOH (100 mL), brine (100 mL), dried (MgSO4) and concentrated. Purification by SiO2 chromatography (10% EtOAc in hexanes) afforded 3-(bromomethyl)-4-[(diphenylmethylidene)amino]-2-(trifluoromethyl)benzonitrile (4.08 g, 95%) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 7.78 (d, J=8.3 Hz, 1H), 7.78-7.11 (m, 10H), 6.91 (d, J=8.6 Hz, 1H), 4.78 (s, 2H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. washwashed with 1N NaOH (100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by SiO2 chromatography (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-87daad9afd114ccbbad0f6908edccd1d
出典データセット
uspto-grants-2011_09
特許番号
US08026262B2

反応ノート

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