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

HRID 1837524Notes

Reaction equation

HRID 1837524 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-dichloro-phenyl)pent-4-yn-1-ol, 13.7 g (82%); NMR (CDCl3) δ1.9 (m,2H), 2.6 (t,2H), 3.85 (t,2H), 7.2 (dd,1 H), 7.28 (m,1 H), 7.4 (d,2H).

Workup

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

Sources & evidence

ORD record
ord-337cbd7de6c34e8b882a5fd4356b540b
Source dataset
uspto-grants-2004_08
Patent number
US06784184B2

Reaction notes

Loading…