Hydrogen Bromide → 2-(4-Chlorophenyl)pyrimidin-5-ol

HRID 2060252Notes

Reaction equation

HRID 2060252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14]C)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.Br>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11]([OH:14])=[CH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 593221882-(4-Chloro-phenyl)-5-methoxy-pyrimidine

Product 1

HCID 593221782-(4-Chlorophenyl)pyrimidin-5-olYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 2-(4-chloro-phenyl)-5-methoxy-pyrimidine (100 mg, 0.45 mmol) was added hydrogen bromide in acetic acid (3 mL of a 33% by weight solution). The resulting mixture was stirred at reflux for 4 hours. The mixture was then partitioned between diethyl ether (25 mL) and saturated sodium hydrogen carbonate solution (25 mL). The organics were further washed with water (25 mL), brine (25 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting precipitate was washed with pentane (10 mL) and then dried under reduced pressure to afford the title compound as a white solid in 88% yield, 82 mg.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe mixture was then partitioned between diethyl ether (25 mL) and saturated sodium hydrogen carbonate solution (25 mL)
  3. washThe organics were further washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting precipitate was washed with pentane (10 mL)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-4c9237b4d7414fb4be6d04c7ce176153
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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