Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 17943

반응식

HRID 17943 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>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

참가 물질

5

반응물 3

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

생성물 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrile수율 55%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d109f8eb30c24670a9e2b4a7d0590d75
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741321B2

연결된 노트

불러오는 중…