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

HRID 1399931Notes

Reaction equation

HRID 1399931 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1e464639a9944cd8af2b22ee35d04b22
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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