N-bromobutanimide → 4-Bromomethyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

HRID 642304

Reaktionsgleichung

Reaktionsgleichung von HRID 642304
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH3:18])=[O:5])[CH3:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH2:18][Br:19])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 684289834-Bromomethyl-2-phenoxy-thiazole-5-carboxylic acid ethyl esterAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester (1.31 g, 4.99 mmol), N-bromosuccinimide (905 mg, 5.08 mmol) and benzoyl peroxide (60 mg, 0.25 mmol) in carbon tetrachloride (25 mL) was refluxed for 3 h before it was cooled to room temperature and partitioned between dichloromethane and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (1.74 g): MS: (+) m/z 342.0, 344.0 (M+1, 79Br/81Br).

Aufarbeitung

  1. temperaturewas refluxed for 3 h before it
  2. custompartitioned between dichloromethane and water
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eea377ddf9ec4dca8818e281cb7dc51b
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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