3-Allyl-2',6'-dichloro-biphenyl-2-ol → 2',6'-dichloro-3-[(1E)-prop-1-enyl]-1,1'-biphenyl-2-ol

HRID 902302Notes

Reaction equation

HRID 902302 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[C:5]=1[OH:18])[CH:2]=[CH2:3]>ClCCl.CC#N.CC#N.Cl[Pd]Cl>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:6]1[C:5]([OH:18])=[C:4](/[CH:1]=[CH:2]/[CH3:3])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 689666213-Allyl-2',6'-dichloro-biphenyl-2-ol

Product 1

HCID 691184512',6'-dichloro-3-[(1E)-prop-1-enyl]-1,1'-biphenyl-2-olYield 96.1%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-allyl-2′,6′-dichloro-1,1′-biphenyl-2-ol (2.922 g, 10.47 mmol) and bis(acetonitrile)dichloropalladium (II) (136 mg, 0.523 mmol) in anhydrous dichloromethane was heated to reflux under nitrogen for 1 hour. The cooled reaction mixture was then concentrated to a small volume under reduced pressure and directly pre-adsorbed onto silica gel. Purification by flash chromatography using a solvent gradient of 2 to 7.5% ethyl acetate in hexane gave 2.81 g (96%) of 2′,6′-dichloro-3-[(1E)-prop-1-enyl]-1,1′-biphenyl-2-ol as a colorless syrup. HRMS: calcd for C15H12Cl2O, 278.02652. found (EI, M+), 278.0262.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 1 hour
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated to a small volume under reduced pressure and directly pre-adsorbed onto silica gel
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-5d1f010f43a84079bd27a6382ffd8755
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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