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

HRID 902308ノート

反応式

HRID 902308 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6093782Bis(acetonitrile)dichloropalladium触媒2 回HCID 6344Dichloromethane溶媒

実験手順

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]−).

後処理

  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

出典と根拠

ORDレコード
ord-2337e7de2d9e40909ae77bf56c0d49bb
出典データセット
uspto-grants-2008_04
特許番号
US07365095B2

反応ノート

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