Phosphorus tribromide → 4-Bromo-2-(trifluoromethyl)pyrimidine

HRID 2093455Notes

Reaction equation

HRID 2093455 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7](O)[CH:6]=[CH:5][N:4]=1.P(Br)(Br)[Br:13]>>[Br:13][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[N:8]=1

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 178516506HCID 178516506, compound

Product 1

HCID 533023444-Bromo-2-(trifluoromethyl)pyrimidine

Conditions

Temperature
150 °C

Procedure

The 2-(trifluoromethyl)pyrimidin-4-ol (328 mg, 2.0 mmol) and PBr3 (0.188 mL, 2.0 mmol) were mixed and heated at 150° C. for 3 h. The reaction was cooled down and quenched with ice water, extracted with DCM (20 mL×2) to yield the titled compound. The organic phase was concentrated and crude material was purified by preparative TLC with 20% Acetone:Hexane to yield titled compound.

Workup

  1. temperatureThe reaction was cooled down
  2. customquenched with ice water
  3. extractionextracted with DCM (20 mL×2)

Sources & evidence

ORD record
ord-bcec6bd2fc714ad48b39e26ebfcac891
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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