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

HRID 2417567Notes

Reaction equation

HRID 2417567 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>[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

4

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 1

HCID 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-4bb600dfb11b495a82756c7019b3fe33
Source dataset
uspto-grants-1984_09
Patent number
US04469633

Reaction notes

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