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

HRID 2166663
Notes
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Reaction equation

HRID 2166663 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-f2870504f50d4414974ca3cd38a4eb8f
Source dataset
uspto-grants-1983_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04388239

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes