Benzoyl Peroxide → 2,4-Dichloro-6-(chloromethyl)pyrimidine

HRID 426220Notes

Reaction equation

HRID 426220 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][Cl:10])[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 150017782,4-Dichloro-6-(chloromethyl)pyrimidineYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,4-dichloro-6-methylpyrimidine (12.5 g, 76.65 mmol), N-chloro succinimide (12.28 g, 92 mmol), and benzoyl peroxide (2.78 g, 11.5 mmol) in carbon tetrachloride (150 ml) was refluxed for 24 hr. After cooling to room temperature, the mixture was filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, from hexane to 2% ether in hexane) to afford 6 g (40%) of 2,4-dichloro-6-chloromethyl-pyrimidine as a white solid. 1H NMR (200 MHz, CDCl3) δ 4.58 (2H, s), 7.55 (1H, s).

Workup

  1. temperaturewas refluxed for 24 hr
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent, from hexane to 2% ether in hexane)

Sources & evidence

ORD record
ord-9e66d77aa11046c4b33a23e0e82cf8e4
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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