Phosphorus oxybromide → 4-Bromo-5-iodo-2-phenylpyrimidine

HRID 1484848Notes

Reaction equation

HRID 1484848 reaction equation
[I: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]([I: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 178517461HCID 178517461, compound

Product 1

HCID 581694374-Bromo-5-iodo-2-phenylpyrimidineYield 62.5%

Conditions

Temperature
100 °C

Procedure

A mixture of 5-iodo-2-phenylpyrimidin-4-ol (1.97 g, 6.67 mmol, 1.0 eq) and POBr3 (100 g) was heated to 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 organic layer was washed (cold water), dried (Na2SO4), evaporated and purified by silica gel chromatography (hexane as eluent) to afford 4-bromo-5-iodo-2-phenylpyrimidine (1.5 g, 62.5%). LC-MS (m/z): 360.8 [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 organic layer was washed (cold water)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. custompurified by silica gel chromatography (hexane as eluent)

Sources & evidence

ORD record
ord-d84525c4b04c4093b67a2deb77fc8e6c
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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