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

HRID 395375

Reaction equation

HRID 395375 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%); NMR (CDCl3) δ 1.9 (m, 2H), 2.6 (t, 2H), 3.85 (t, 2H), 7.2 (dd, 1H), 7.28 (m, 1H), 7.4 (d, 2H).

Workup

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

Sources & evidence

ORD record
ord-929d5a52771a4fb78e7fade0ed26344a
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Linked notes

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