1,2-Dichloro-3-iodobenzene → HCID 68707622, compound

HRID 2232966Notes

Reaction equation

HRID 2232966 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[Cl:9].[CH2:10]([C:17]#[CH:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N(CC)CC)C.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:18]#[C:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[Cl:9]

Participants

5

Reactant 2

HCID 754591,2-Dichloro-3-iodobenzeneHCID 575753Benzylacetylene

Product 1

HCID 68707622HCID 68707622, compound

Reagents, catalysts & solvents 2

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

Procedure

1,2-Dichloro-3-iodobenzene (4.39 g, 16.1 mmol), benzylacetylene (1.96 g, 16.9 mmol), copper(I) iodide (26 mg, 0.14 mmol) and bistriphenylphosphinepalladium(II)chloride (113 mg, 0.16 mmol) were combined in triethylamine (100 mL) and heated at reflux for 2 hours. The reaction was allowed to cool to room temperature and then was partitioned between saturated sodium chloride and diethylether. The organic phase was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel (eluting with hexane) to provide the title compound. MS (DCI/NH3) m/z 278 (M+NH4)+; 1H NMR (CDCl3) δ 3.90 (s, 2H), 7.13 (t, 1H), 7.2-7.5 (m, 7H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customwas partitioned between saturated sodium chloride and diethylether
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified on silica gel (eluting with hexane)

Sources & evidence

ORD record
ord-84dd033d2fd54e358aa89108595ad803
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

Loading…