N-bromobutanimide → Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

HRID 2121178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121178
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:20])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:17])([F:16])[F:18])(=[O:14])=[O:13]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Produkt 1

HCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(trifluoromethanesulfonyloxy)-4-methylbenzoic acid methyl ester (19.6 g, 65.8 mmol), prepared as in Example 204A, in 250 mL CCl4 was added N-bromosuccinimide (12.29 g, 69.1 mmol) followed by 2,2′-azobisisobutyronitrile (108 mg, 0.658 mmol) and the reaction was heated to reflux. After 16 hours, the reaction was evaporated and the residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes) to give 19.9 g (80%) of 2-(trifluoromethanesulfonyloxy)-4-bromomethylbenzoic acid methyl ester as a yellow oil.

Aufarbeitung

  1. temperaturethe reaction was heated to reflux
  2. customthe reaction was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-021253110724429d8d88c46e39a6e0e1
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693123B2

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