Diethyl Ether → 4-Bromomethyl-2-(4-trifluoromethylphenyl)pyrimidine

HRID 22255Notes

Reaction equation

HRID 22255 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:3]=1.[Br:18]Br.CCOCC>C(O)(=O)C>[Br:18][CH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 194302744-Methyl-2-(4-trifluoromethylphenyl)pyrimidine

Product 1

HCID 194302394-Bromomethyl-2-(4-trifluoromethylphenyl)pyrimidineYield 82.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-methyl-2-(4-trifluoromethylphenyl)pyrimidine (3 g) and bromine (2.11 g) in 20 ml of acetic acid was warmed to 80° C. for 1 hour, and then allowed to cool to room temperature. Ether (10 ml) was added., and the precipitate filtered off and washed with ether, giving 3.3 g of 4-bromomethyl-2-(4-trifluoromethylphenyl)pyrimidine, m.p. 125° C.

Workup

  1. temperatureto cool to room temperature
  2. filtration, and the precipitate filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-673546b0a9354c379910b70d7eca61f5
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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