Phosphorus oxybromide → 4,5-Dibromo-2-phenylpyrimidine

HRID 1484841Notes

Reaction equation

HRID 1484841 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.P(Br)(Br)([Br:17])=O>>[Br:17][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=1

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178517460HCID 178517460, compound

Product 1

HCID 581693934,5-Dibromo-2-phenylpyrimidineYield 70.5%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-phenylpyrimidin-4-ol (1.67 g, 6.67 mmol, 1.0 equiv.) and POBr3 (100 g) was heated at 100° C. for 8 hours. The solution was cooled down to 55° C. and poured into ice-water while stirring vigorously. The mixture was maintained below 25° C. during the quench. The reaction mixture was extracted with CH2Cl2. The combined organic layer was washed (cold water), dried (Na2SO4), evaporated and the residue was purified by silica gel chromatography (hexane) to afford 4,5-dibromo-2-phenyl pyrimidine (1.3 g, 70.5%). LC-MS (m/z): 315.1 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 7.47-7.50 (m, 3H), 8.37-8.40 (m, 2H), 8.91 (s, 1H).

Workup

  1. temperatureThe solution was cooled down to 55° C.
  2. temperatureThe mixture was maintained below 25° C. during the quench
  3. extractionThe reaction mixture was extracted with CH2Cl2
  4. washThe combined organic layer was washed (cold water)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customthe residue was purified by silica gel chromatography (hexane)

Sources & evidence

ORD record
ord-123df0f1dae84c2f9c70f449b982564d
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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