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

HRID 2101993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101993
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5a4bbc874fac475daf83161561a90991
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572820B2

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