Boron tribromide → 5-(p-Hydroxyphenoxy)pyrimidine

HRID 1413052

Reaction equation

HRID 1413052 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C:8]2[CH:13]=[N:12][CH:11]=[N:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20292632HCID 20292632, compound

Product 1

HCID 129406205-(p-Hydroxyphenoxy)pyrimidineYield 5.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(p-Methoxyphenoxy)pyrimidine (7.7 g) was dissolved in dichloromethane and the solution, maintained at a temperature of -70° to -78° C., was treated by the dropwise addition of boron tribromide (7 ml). The stirred solution was allowed to warm to room temperature and after standing overnight the dichloromethane solution was washed with a cold saturated aqueous solution of sodium bicarbonate (100 ml). The dichloromethane solution was then dried, treated with charcoal and the solvent removed by distillation under reduced pressure. The residue was washed with diethyl ether to give 5-(p-hydroxyphenoxy)pyrimidine (0.4 g) m.p. 158° C. which was characterised by p.m.r. spectroscopy.

Workup

  1. temperaturethe solution, maintained at a temperature of -70° to -78° C.
  2. washthe dichloromethane solution was washed with a cold saturated aqueous solution of sodium bicarbonate (100 ml)
  3. dry with materialThe dichloromethane solution was then dried
  4. additiontreated with charcoal
  5. customthe solvent removed by distillation under reduced pressure
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-2ca862c074ec497ea11bc0de5bcc83e4
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Linked notes

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