Benzoyl Peroxide → 2-Chloro-4-(chloromethyl)pyrimidine

HRID 426127Notes

Reaction equation

HRID 426127 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Cl:9]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]([CH2:8][Cl:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 116296072-Chloro-4-methylpyrimidine

Product 1

HCID 216981282-Chloro-4-(chloromethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The mixture of 2-Chloro-4-methyl-pyrimidine (51) (6.48 g, 50 mmol), N-chloro succinimide (8.0 g, 60 mmol), and benzoyl peroxide (2.42 g, 10 mmol) in carbon tetrachloride (100 ml) was refluxed for 22 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:2)) to afford 3.3 g (40%). 1H NMR (200 MHz, CDCl3) δ: 4.57 (2H, s), 7.50 (1H, d, J=5.2 Hz), 8.65 (1H, d, J=5.2 Hz).

Workup

  1. temperaturewas refluxed for 22 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:2))
  5. customto afford 3.3 g (40%)

Sources & evidence

ORD record
ord-caead1e9330642eb9d3766dc7b94e667
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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