Benzoyl Peroxide → 4-(3-Bromomethyl-5-methyl-phenoxy)-2,6-dichloro-5-isopropyl-pyrimidine

HRID 426197Notes

Reaction equation

HRID 426197 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[C:4]([O:12][C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)[N:3]=1.C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.[W]>[Br:28][CH2:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([CH3:20])[CH:16]=1)[O:12][C:4]1[C:5]([CH:9]([CH3:10])[CH3:11])=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 189252522,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine

Product 1

HCID 591846894-(3-Bromomethyl-5-methyl-phenoxy)-2,6-dichloro-5-isopropyl-pyrimidineYield 66.2%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,4-dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine (9.72 g, 31 mmol), NBS (5.56 g, 31 mmol), and benzoyl peroxide (0.756 g, 3.1 mmol) in carbon tetrachloride (60 ml) was refluxed for 3 hr. under a light of 500 W tungsten lamp. After cooling to room temperature, the reaction mixture was filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:19)) to afford 8 g (62%) of a white solid. m.p. 98-101° C.; 1H NMR (200 MHz, CDCl3) δ 1.41 (6H, d, J=7.2 Hz), 2.38 (3H, s), 3.59 (1H, m), 4.47 (2H, s), 6.86 (1H, s), 6.97 (1H, s), 7.13 (1H, s).

Workup

  1. temperaturewas refluxed for 3 hr
  2. filtrationthe reaction mixture was filtered
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:19))

Sources & evidence

ORD record
ord-fa6096908dd44a7fba03f6e3aa823d24
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…