Sodium Cyanide → 5-(3-Bromophenyl)pentanenitrile

HRID 2240993노트

반응식

HRID 2240993 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[C-:23]#[N:24].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 57435871Toluene-4-sulfonic acid 4-(3-bromophenyl)butyl ester

생성물 1

HCID 574358725-(3-Bromophenyl)pentanenitrile수율 78.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of toluene-4-sulfonic acid 4-(3-bromophenyl)butyl ester (2.3 g, 6 mmol) and powdered sodium cyanide (0.65 g, 13 mmol) in DMSO was heated up to 80° C., stirred for 1.5 hours and monitored by NMR. When the reaction was complete, the reaction mixture was cooled to room temperature, diluted with H2O and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of this residue on silica gel (ISCO) using (hexanes/EtOAC 9.5/0.5) as the eluting solvent gave 5-(3-bromo-phenyl)pentanenitrile as a colorless oil (1.12 g, 78% yield). m/e (M)+ 237; 1H NMR (400 MHz, DMSO-d6) δ ppm, 2.63-2.65 (m, 2H), 2.75-2.78 (m, 2H), 2.35-2.38 (m, 2H), 2.60-2.63 (m, 2H), 7.05-7.10 (m, 2H), 7.25-7.28 (m, 2H).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of this residue on silica gel (ISCO)

출처 및 근거

ORD 기록
ord-bb31ccb7f23a42bc9a96fc1036857740
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723368B2

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