1,4-Dichlorobenzene → HCID 15274145, compound

HRID 1293506Notes

Reaction equation

HRID 1293506 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[CH2:9]([Mg]Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CCOCC>[CH2:9]([C:2]1[CH:7]=[CH:6][C:5]([CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 46851,4-DichlorobenzeneHCID 178444609HCID 178444609, compound

Product 1

HCID 15274145HCID 15274145, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A 2 L round-bottomed flask is charged with 1,4-dichlorobenzene (118 g, 0.80 mol), [1,3 -bis(diphenylphosphino)propane]Ni(II) chloride (500 mg, 0.9 mmol), and dry ether (600 mL). The mixture is cooled to 0° C. and a 2 M solution of n-hexylmagnesium bromide in ether (1 L) is added dropwise. The cooling bath is removed, and the solution is slowly heated to reflux and allowed to boil for 24 h. The mixture is cooled to 0° C. and diluted with water (50 mL) and then with a 2 M aqueous hydrochloric acid solution (500 mL). The aqueous layer is separated, extracted with ether (2×200 mL), and the combined organic layers are washed with water (100 mL) and dried over magnesium sulfate. The solvent is removed in vacuo and the product is purified by distillation.

Workup

  1. customThe cooling bath is removed
  2. temperaturethe solution is slowly heated
  3. temperatureto reflux
  4. temperatureThe mixture is cooled to 0° C.
  5. additiondiluted with water (50 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with ether (2×200 mL)
  8. washthe combined organic layers are washed with water (100 mL)
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent is removed in vacuo
  11. distillationthe product is purified by distillation

Sources & evidence

ORD record
ord-e677b19f69764104b204086960a6afc6
Source dataset
uspto-grants-2007_07
Patent number
US07238771B2

Reaction notes

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