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

HRID 902308Notes

Reaction equation

HRID 902308 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

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]−).

Workup

  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

Sources & evidence

ORD record
ord-2337e7de2d9e40909ae77bf56c0d49bb
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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