1-Chloro-2-fluoro-4-iodobenzene → 1-Chloro-2-fluoro-4-[(4-pentylphenyl)ethynyl]benzene

HRID 1613528Notes

Reaction equation

HRID 1613528 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:14][C:15]1[CH:16]=[C:17](I)[CH:18]=[CH:19][C:20]=1[Cl:21]>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.[Cu]I.C(NCC)C>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:17]2[CH:18]=[CH:19][C:20]([Cl:21])=[C:15]([F:14])[CH:16]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 2

HCID 27365631-Chloro-2-fluoro-4-iodobenzeneHCID 27751311-Ethynyl-4-pentylbenzene

Product 1

HCID 157452301-Chloro-2-fluoro-4-[(4-pentylphenyl)ethynyl]benzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

0.2 mmol of Pd(PPh3)2Cl2 and 0.1 mmol of CuI are added to a mixture of 0.01 mol of 4-pentylphenylacetylene, 0.01 mol of 3-fluoro-4-chloro-iodobenzene and 40 ml of diethylamine at room temperature and stirred for 12 hours. After completion of the reaction, the suspension is filtered, and the filtrate is concentrated by evaporation. Purification by chromatography and/or crystallization gives 4-pentyl-3'-fluoro-4'-chloro tolan having C 49.6° I.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe suspension is filtered
  3. concentrationthe filtrate is concentrated by evaporation
  4. customPurification
  5. customby chromatography and/or crystallization

Sources & evidence

ORD record
ord-27b81805cbca4584a94a315c6f563575
Source dataset
uspto-grants-1993_03
Patent number
US05194178

Reaction notes

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