4-Pentyn-1-ol → 5-(2,5-Dichlorophenyl)pent-4-yn-1-ol

HRID 982735

Reaction equation

HRID 982735 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1I.[CH2:10]([OH:15])[CH2:11][CH2:12][C:13]#[CH:14]>C(NCC)C.ClCCl.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:14]#[C:13][CH2:12][CH2:11][CH2:10][OH:15]

Participants

6

Reactant 2

HCID 793464-Pentyn-1-olHCID 1224521,4-Dichloro-2-iodobenzene

Product 1

HCID 223207595-(2,5-Dichlorophenyl)pent-4-yn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

A solution of 1,4-dichloro-2-iodobenzene (20.0 g, 73.3 mmol), 4-pentyn-1-ol (6.17 g, 73.3 mmol), bistriphenylphosphine(Pd II) chloride (1.03 g, 1.47 mmol), and copper(I) iodide (0.14 g, 0.733 mmol) in 400 ml of diethylamine was stirred under nitrogen for three days. This was diluted with dichloromethane and the oily layer was adsorbed onto silica gel and eluted with hexanes-ethyl acetate (5:1)to give 5-(2,5-dichlorophenyl)-pent-4-yn-1-ol, 13.7 g (82%).

Workup

  1. washeluted with hexanes-ethyl acetate (5:1)to

Sources & evidence

ORD record
ord-9969cf388392435b81fa542945a2bcf1
Source dataset
uspto-grants-2005_03
Patent number
US06861445B2

Linked notes

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