Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 62596

반응식

HRID 62596 반응식
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 88310(3-Methoxyphenyl)acetonitrile

생성물 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrile수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(3-methoxyphenyl)acetonitrile (2 g; 13.59 mmol) in 13 mL of dry dichloromethane (DCM) cooled at 0° C. under an inert atmosphere, a 1M solution of BBr3 in DCM (28.54 mmol; 28.54 mL) is slowly added dropwise. The mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into ice, water is added and the organic phase is extracted three times with dichloromethane, washed with brine and dried over anhydrous Na2SO4. After evaporation, the crude mixture is purified by flash-chromatography on silica gel using petroleum ether/EtAc (80/20) as an eluant, affording 1.28 g (71%) of 2-(3-hydroxyphenyl)acetonitrile.

후처리

  1. additionis added
  2. extractionthe organic phase is extracted three times with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation
  6. customthe crude mixture is purified by flash-chromatography on silica gel

출처 및 근거

ORD 기록
ord-421976812b0e42e5bece4cc9233e266c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447029B2

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