Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 62596

反応式

HRID 62596 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrile収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-421976812b0e42e5bece4cc9233e266c
出典データセット
uspto-grants-2016_09
特許番号
US09447029B2

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