Benzoyl Peroxide → 4-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

HRID 270140

Reaktionsgleichung

Reaktionsgleichung von HRID 270140
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27372104-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 179517684-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a 2-L round-bottom flask equipped with an mechanical overhead stirrer, a reflux condenser and a N2inlet was added ethyl 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate (85g, 0.27moles, 1.0eq) and dry carbon tetrachloride (750ml, 0.38M). Freshly recrystallized N-bromo succinimide (52.72g, 1.1eq) was added as a solid, Benzoyl peroxide (6.5g, 10mol %) was added at room temperature all at once as a solid, and the reaction mixture was refluxed for 5hrs. The reaction was monitored by 1H NMR and was determined to be composed of a 9:1mixture of mono-bromination product (i.e. desired product) and di-bromination product with a 90% conversion. After cooling to 0° C. (to precipitate out the succinimide) the reaction was filtered through Celite and the solvent was removed under reduced pressure to yield a brown oil. The oil was crystallized using hexanes to yield 100g (94%) of an off-white product of 90% purity.

Aufarbeitung

  1. customTo a 2-L round-bottom flask equipped with an mechanical overhead stirrer, a reflux condenser
  2. additionwas added at room temperature all at once as a solid
  3. temperaturethe reaction mixture was refluxed for 5hrs

Quellen und Nachweise

ORD-Eintrag
ord-70b1c34ed7624076a507fc4978cd36af
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449468B2

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