Thionyl Chloride → 5-(Chloromethyl)-2-cyclohexylbenzonitrile

HRID 2040547

반응식

HRID 2040547 반응식
[CH:1]1([C:7]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:8]=2[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O>>[Cl:19][CH2:15][C:12]1[CH:13]=[CH:14][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 580205132-Cyclohexyl-5-(hydroxymethyl)benzonitrile

생성물 1

HCID 672113535-(Chloromethyl)-2-cyclohexylbenzonitrile수율 89.4%

반응 조건

온도
50 °C

실험 절차

To 2-cyclohexyl-5-(hydroxymethyl)benzonitrile (190.5 mg, 0.885 mmol) was added thionyl chloride (5.0 mL, 68.1 mmol). The mixture was heated at 50° C. for 2 h and then room temperature overnight. The mixture was poured into an ice and stirred for 5 min. The mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide the title compound as a white solid (184.9 mg). LCMS m/z=234.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.31 (m, 1H), 1.40-1.52 (m, 4H), 1.76-1.82 (m, 1H), 1.83-1.92 (m, 4H), 2.93-3.03 (m, 1H), 4.55 (s, 2H), 7.37 (d, J=8.08 Hz, 1H), 7.55 (dd, J=8.02, 1.83 Hz, 1H), 7.62 (d, J=1.64 Hz, 1H).

후처리

  1. customroom temperature overnight
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cc83b98607d64fe5902a247ce413cb60
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580841B2

연결된 노트

불러오는 중…