Water → 4-[(5-Bromo-2-pyrimidinyl)oxy]phenol

HRID 2295949ノート

反応式

HRID 2295949 の反応式
[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]=1

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 45415135-bromo-2-(4-methoxyphenoxy)pyrimidine

生成物 1

HCID 133366404-[(5-Bromo-2-pyrimidinyl)oxy]phenol収率 92.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  1. temperaturethe temperature of the solution being maintained at -65° to -75° C
  2. additionOn completion of the addition the reaction mixture
  3. customto rise slowly to room temperature
  4. customthe methylene chloride removed
  5. temperatureby heating the mixture on a water bath
  6. temperatureThe aqueous suspension was cooled to a temperature of 20° C.
  7. filtrationthe solid was collected by filtration
  8. washwashed with water
  9. customrecrystallised from methanol/water

出典と根拠

ORDレコード
ord-262a7d94efc04ad4bb8c16f2400f7347
出典データセット
uspto-grants-1984_01
特許番号
US04427437

反応ノート

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