1,4-Dichlorobenzene → Benzene, 1-butyl-4-chloro-

HRID 485959Notes

Reaction equation

HRID 485959 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][CH:4]=[C:3](Cl)[CH:2]=1.[CH2:9]([Mg]Cl)[CH2:10][CH2:11][CH3:12]>CCOCC>[CH2:9]([C:3]1[CH:2]=[CH:1][C:6]([Cl:7])=[CH:5][CH:4]=1)[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 46851,4-DichlorobenzeneHCID 178418265HCID 178418265, compound

Product 1

HCID 524314Benzene, 1-butyl-4-chloro-Yield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 2.00 g (13.61 mmoles) of p-dichlorobenzene, and 0.050 g of [NiCltriphos]PF6 in 20 mL of ether at -78° C. was added 7.0 mL (14 mmoles) of 2M nBuMgCl in ether. After refluxing overnight and workup with NH4Cl solution, the residue (602 mg of 1.698 g) was flash-chromatographed with 5% EtOAc/hexane on silica gel to give 542 mg (67%) of 1-butyl-4-chlorobenzene. 1H NMR (200 MHz, CDCl3): δ7.22 (m,2H), 7.05 (m,2H), 2.59 (t, J=5.5 Hz, 2H), 1.58 (m, 2H), 1.34 (m,2H) 0.95 (t, J=5.2 Hz, 3H). IR(neat): 2958s, 2930s, 2859s, 1492s, 1466m, 1407m, 1901s, 1016s cm-1.

Workup

  1. temperatureAfter refluxing overnight
  2. customworkup with NH4Cl solution, the residue (602 mg of 1.698 g) was flash-chromatographed with 5% EtOAc/hexane on silica gel

Sources & evidence

ORD record
ord-2053e988973941d182cf3bdd7c51631a
Source dataset
uspto-grants-1985_08
Patent number
US04538003

Reaction notes

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