Water → 4-[(5-Bromo-2-pyrimidinyl)oxy]phenol
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[N:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
5-Bromo-2-(4-methoxyphenoxy)pyrimidine (2.4 g) was dissolved in methylene chloride (50 ml) and the solution cooled to a temperature of -70° C. Boron tribromide (12.7 g) was added dropwise to the stirred solution, the temperature of the solution being maintained at -65° to -75° C. On completion of the addition the reaction mixture was stirred for a further one hour at a temperature of -65° to -75° C. and then the temperature of the reaction mixture was allowed to rise slowly to room temperature. The reaction mixture was added cautiously, in small portions, to water and the methylene chloride removed by heating the mixture on a water bath. The aqueous suspension was cooled to a temperature of 20° C., the solid was collected by filtration, washed with water and recrystallised from methanol/water to give 4-(5-bromo-2-pyrimidyloxy)phenol (2.1 g), m.p. 178° C.
Workup
- temperaturethe temperature of the solution being maintained at -65° to -75° C
- additionOn completion of the addition the reaction mixture
- customto rise slowly to room temperature
- customthe methylene chloride removed
- temperatureby heating the mixture on a water bath
- temperatureThe aqueous suspension was cooled to a temperature of 20° C.
- filtrationthe solid was collected by filtration
- washwashed with water
- customrecrystallised from methanol/water
Sources & evidence
- ORD record
- ord-6269c9f3522b41529dc867cd00a8edb7
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04248618
Reaction notes
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