Ethyl Bromide → Ethyl 4-cyanophenyl sulfide

HRID 911283노트

반응식

HRID 911283 반응식
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([S:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH3:12]

참가 물질

5

반응물 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5850584-Thiobenzonitrile

생성물 1

HCID 21262891Ethyl 4-cyanophenyl sulfide수율 83%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Combine 4-mercapto-benzonitrile (0.4 g, 2.96 mmol), bromoethane (1.4 mL, 8.88 mmol) and potassium carbonate (3.3 g, 23.7 mmol) in anhydrous DMF (7 mL) and heat at 60° C. for 17 h. Cool the reaction mixture to ambient temperature and partition between brine (20 mL) and EtOAc (20 mL). Separate the organic layer, dry over anhydrous Na2SO4 and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the desired intermediate as a colorless oil (0.4 g, 83%).

후처리

  1. custompartition between brine (20 mL) and EtOAc (20 mL)
  2. customSeparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

출처 및 근거

ORD 기록
ord-c3aa0a5f7356458d8baf58e3291c277f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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