Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 17943

反応式

HRID 17943 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>C(Cl)Cl>[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 55%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (3-methoxyphenyl)acetonitrile (150 g, 1.03 mol) in CH2Cl2 (1000 mL) was added BBr3 (774 g, 3.09 mol) dropwise at −70° C. The mixture was stirred and warmed to room temperature slowly. Water (300 mL) was added at 0° C. The resulting mixture was extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude residue was purified by column (Petroleum Ether/EtOAc 10:1) to give (3-hydroxyphenyl)acetonitrile (75.0 g, 55%). 1H NMR (CDCl3, 300 MHz) δ 7.18-7.24 (m, 1H), 6.79-6.84 (m, 3H), 3.69 (s, 2H).

後処理

  1. extractionThe resulting mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe crude residue was purified by column (Petroleum Ether/EtOAc 10:1)

出典と根拠

ORDレコード
ord-d109f8eb30c24670a9e2b4a7d0590d75
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

関連ノート

読み込み中…