HCID 68965446, compound → HCID 69116794, compound

HRID 902349Notes

Reaction equation

HRID 902349 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:5]=1[OH:18])[CH:2]=[CH2:3]>C(Cl)Cl.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]=[CH:2][CH3:3])=[C:5]([OH:18])[C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Participants

4

Reactant 1

HCID 68965446HCID 68965446, compound

Product 1

HCID 69116794HCID 69116794, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 178424406HCID 178424406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-allyl-6-chloro-2′-methylbiphenyl-2-ol (2.0 g, 7.7 mmol) in methylene chloride (70 mL) was added dichlorobis(acetonitrile)palladium (II) (0.22 g, 0.84 mmol). The resulting mixture was refluxed overnight. The solvent was removed under reduced pressure. Purification by ISCO using a solvent gradient of 5 to 20% ethyl acetate in hexanes provided 1.0 g (50%) of 6-chloro-2′-methyl-3-(prop-1-enyl)biphenyl-2-ol as a colorless oil.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. customPurification by ISCO

Sources & evidence

ORD record
ord-82730732da564155bffb76e019aa3d86
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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