Propargyl alcohol → 3-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne

HRID 1074869Notes

Reaction equation

HRID 1074869 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].[CH2:18]([OH:21])[C:19]#[CH:20]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:21][CH2:18][C:19]#[C:20][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][C:6]=1[C:7](=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 12948263(5-Chloro-2-iodophenyl)(2-fluorophenyl)methanone

Product 1

HCID 128416493-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 0.37 g (0.5 mmole) of dichlorobis(triphenylphosphine)palladium II, 70 mg (0.35 mmole) of cuprous iodide, 36.1 g (0.1 mole) of 5-chloro-2'-fluoro-2-iodobenzophenone and 12 ml (0.2 mole) of propargyl alcohol in 200 ml of diethylamine was stirred at room temperature for 4 days. The mixture was concentrated at reduced pressure and the residue was partitioned between ether and water. The ether layer was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to give the product as an amber oil.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure
  2. customthe residue was partitioned between ether and water
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-b11fa6956d81484295a36248f6858579
Source dataset
uspto-grants-1983_07
Patent number
US04394311

Reaction notes

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