Phenol → 4-Bromo-2-phenoxybenzonitrile

HRID 733045노트

반응식

HRID 733045 반응식
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]C1C=CC=CC=1.[Br:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20](F)[CH:19]=1.[OH-].[Na+]>CN(C=O)C>[Br:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:19]=1

참가 물질

7

반응물 5

HCID 996PhenolHCID 14798Sodium HydroxideHCID 24758Sodium hydride2회HCID 119047PhenolateHCID 7360294-Bromo-2-fluorobenzonitrile

생성물 1

HCID 574366654-Bromo-2-phenoxybenzonitrile수율 90.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (12 g, 300 mmol) (60% by wt) was weighed into a flask and washed free of oil with several hexane rinsings. The hexanes were decanted and discarded and DMF was added to the flask. A DMF-solution of phenol (23.5 g, 250 mmol in 100 mL DMF) was added dropwise to the NaH mixture and stirred at room temperature. To the phenoxide was added a solution of 4-bromo-2-fluoro-benzonitrile (50 g, 250 mmol in 100 mL DMF), dropwise. Upon complete addition, the reaction was refluxed for 20 h. The reaction was cooled to room temperature, and poured into cold 1 N NaOH. A fine, tan precipitate formed and was collected by vacuum filtration to give 62.04 g (226 mmol) of Compound 1a. MS m/z (MH+) 277.

후처리

  1. washwashed free of oil with several hexane rinsings
  2. customThe hexanes were decanted
  3. additionDMF was added to the flask
  4. additionUpon complete addition
  5. temperaturethe reaction was refluxed for 20 h
  6. temperatureThe reaction was cooled to room temperature
  7. customA fine, tan precipitate formed
  8. filtrationwas collected by vacuum filtration

출처 및 근거

ORD 기록
ord-422dba2923d6435387a627de02124800
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589103B2

반응 노트

불러오는 중…