Benzoyl Peroxide → 5-Bromo-2-(bromomethyl)pyrimidine

HRID 1255804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255804
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.C1C(=O)N([Br:16])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:16])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

Produkt 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-methylpyrimidine (100 mg, 0.58 mmol), NBS (103 mg, 0.58 mmol), dibenzoyl peroxide (10 mg, 0.04 mmol) in tetrachloromethane (10 mL) was refluxed for 36 h. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 1% v/v) to give 5-Bromo-2-(bromomethyl)pyrimidine (70 mg, 48%) as a white solid. 1HNMR (400 MHz, CDCl3) δ 4.49 (s, 2H), 8.72 (s, 2H).

Aufarbeitung

  1. temperaturewas refluxed for 36 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 1% v/v)

Quellen und Nachweise

ORD-Eintrag
ord-baae7a979bc3473ea1959598bfcadcce
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461157B2

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