2-Allyl-6-bromo-4-fluorophenol → 2-bromo-4-fluoro-6-[(1E)-prop-1-enyl]phenol

HRID 902308노트

반응식

HRID 902308 반응식
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([Br:11])[C:5]=1[OH:12])[CH:2]=[CH2:3]>ClCCl.CC#N.CC#N.Cl[Pd]Cl>[Br:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:4](/[CH:1]=[CH:2]/[CH3:3])[C:5]=1[OH:12]

참가 물질

4

반응물 1

HCID 623681612-Allyl-6-bromo-4-fluorophenol

생성물 1

HCID 691167832-bromo-4-fluoro-6-[(1E)-prop-1-enyl]phenol수율 90.2%

시약·촉매·용매 2

HCID 6093782Bis(acetonitrile)dichloropalladium촉매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-allyl-6-bromo-4-fluorophenol (7.14 g, 0.0309 mol) in anhydrous dichloromethane (100 mL) at room temperature under nitrogen was added bis(acetonitrile)dichloropalladium (II) (0.4 g, 1.54 mmol) and the reaction mixture heated to reflux for 1 hour. Additional bis(acetonitrile)dichloropalladium (II) (0.1 g, 0.39 mmol) was added and heating to reflux continued for 1 additional hour. The cooled reaction mixture was then concentrated under reduced pressure to afford a brown semi-solid. Purification by flash chromatography using a solvent gradient of 0 to 2% ethyl acetate in hexane gave 6.44 g (90%) of 2-bromo-4-fluoro-6-[(1E)-prop-1-enyl]phenol as a white solid. MS (ESI) m/z 229 ([M−H]−).

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 1 hour
  3. temperatureheating
  4. temperatureto reflux
  5. customThe cooled reaction mixture
  6. concentrationwas then concentrated under reduced pressure
  7. customto afford a brown semi-solid
  8. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-2337e7de2d9e40909ae77bf56c0d49bb
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

반응 노트

불러오는 중…