Sulfuric Acid → 4-Bromo-3-(trifluoromethyl)phenol

HRID 725804노트

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HRID 725804 반응식
[Br:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[OH:13]S(O)(=O)=O.N([O-])=O.[Na+]>O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:13])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10]

참가 물질

5

반응물 3

HCID 1118Sulfuric Acid2회HCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

생성물 1

HCID 222773074-Bromo-3-(trifluoromethyl)phenol

시약·촉매·용매 1

HCID 962Water용매2회

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온도
0 °C

실험 절차

4-Bromo-3-trifluoromethylaniline (48 g, 0.2 mol) was treated with water (300 ml) and concentrated H2SO4 (36 ml) at 60° C. for 1 hour. The resulting suspension was cooled in an ice bath and treated with sodium nitrite (16 g, 0.23 mol) in water (30 ml) maintaining the temperature of the reaction mixture below 10° C. The resulting solution was stirred at 0° C. for 1 hour, and then added portionwise, over 1 hour, to a 25% H2SO4 aqueous solution (160 ml) whilst steam distilling. After collecting approximately 1 liter of distillate, the aqueous distillate was extracted with ether and the organic solution dried using MgSO4, filtered and concentrated. The product, 4-bromo-3-trifluoromethylphenol, was obtained by distillation under reduced pressure. Yield 18.0 g (37%); boiling point 68-71/1 mmHg.

후처리

  1. temperatureThe resulting suspension was cooled in an ice bath
  2. temperaturemaintaining the temperature of the reaction mixture below 10° C
  3. distillationdistilling
  4. distillationAfter collecting approximately 1 liter of distillate
  5. extractionthe aqueous distillate was extracted with ether
  6. customthe organic solution dried
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a1bd8a00faa462fbf15b455dc582202
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05707995

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