Benzoyl Peroxide → HCID 86673424, compound

HRID 2362386Notes

Reaction equation

HRID 2362386 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:16])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][Br:16])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 109429282-Bromo-4-methylpyrimidine

Product 1

HCID 86673424HCID 86673424, compoundYield 20.04%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-bromo-4-methylpyrimidine (1.5 g, 8.67 mmol) in CCl4 (15 mL) was added NBS (3.39 g, 19.07 mmol) and benzoyl peroxide (0.476 g, 1.907 mmol) then it was heated to 80° C. After 48 hours, the reaction mixture was cooled to ambient temperature and filtered. The black solid was discarded and liquid was concentrated to brown solid which was purified by column chromatography (10% EtOAc/Hex) to obtained a yellow solid of 2-bromo-4-(bromomethyl)pyrimidine (437.6 mg, 1.737 mmol, 20.04% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.74 (d, J=4.9 Hz, 1H), 7.75 (d, J=4.9 Hz, 1H), 4.66 (s, 2H)), Mass spec.: 252.9 (MH)+.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationliquid was concentrated to brown solid which
  4. customwas purified by column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-2ab2e68ef90f449f9b8994e9557aaa20
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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