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

HRID 1413042노트

반응식

HRID 1413042 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6269c9f3522b41529dc867cd00a8edb7
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04248618

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