7-Octyn-1-ol → 8-(3,4-Dichlorophenyl)oct-7-yn-1-ol

HRID 2228893Notes

Reaction equation

HRID 2228893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10]([OH:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17]>[Cu]I.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]#[C:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 701007-Octyn-1-olHCID 88591Benzene, 1,2-dichloro-4-iodo-

Product 1

HCID 184701968-(3,4-Dichlorophenyl)oct-7-yn-1-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3,4-dichloroiodobenzene (2.16 g), oct-7-yn-1-ol (1.20 g), tetrakis (triphenylphosphine)palladium (0) (0.185 g), copper (I) iodide (0.046 g) and triethylamine (15 ml) was stirred at room temperature for 16 h. The solid was filtered off and the filtrate evaporated under reduced pressure. The residual oil was dissolved in ethyl acetate (15 ml) and washed with water (10 ml), 2M hydrochloric acid (2×10 ml) and brine (10 ml). Drying over magnesium sulfate and removal of the solvent under reduced pressure gave an oil that was purified by flash chromatography on silica gel using dichloromethane as eluent. This gave 8-(3,4-dichlorophenyl)oct-7-yn-1-ol (1.89 g). 1H-NMR (CDCl3) δ 1.2-1.75 (8H, m), 2.40 (2H, t), 3.66 (2H, t), 7.19 (1H, dd), 7.35 (1H, d) and 7.47 (1H, dd).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate evaporated under reduced pressure
  3. dissolutionThe residual oil was dissolved in ethyl acetate (15 ml)
  4. washwashed with water (10 ml), 2M hydrochloric acid (2×10 ml) and brine (10 ml)
  5. dry with materialDrying over magnesium sulfate and removal of the solvent under reduced pressure
  6. customgave an oil that
  7. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bb45b933ad6140a1bd0309401c015a5d
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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