Benzoyl Peroxide → 4-(Bromomethyl)-2-chloro-1-(trifluoromethyl)benzene

HRID 1961696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1961696
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12])[CH2:8][Br:13]

Komponenten

6

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27366192-Chloro-4-methylbenzotrifluoride

Produkt 1

HCID 235127654-(Bromomethyl)-2-chloro-1-(trifluoromethyl)benzeneAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-4-methyl-1-trifluoromethylbenzene 26 (0.20 g, 1 mmol), N-bromosuccinimide (0.17 g, 1 mmol) and benzoyl peroxide (7.4 mg, 0.03 mmol) in carbon tetrachloride (2 mL) was heated to reflux for 2 hours. Another portion of benzoyl peroxide (20 mg, 0.08 mmol) was added. The mixture was heated to reflux for another 0.5 hours. The reaction mixture was further stirred at room temperature for 16 hours. The solid was removed by filtration. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica, using petroleum ether as eluent, to give 0.22 g (80%) of Compound 27.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was heated
  4. temperatureto reflux for another 0.5 hours
  5. customThe solid was removed by filtration
  6. customThe solvent was removed under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-53866a1148144b11bd6d8c80e4783603
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415357B2

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