1,4-Dichlorobenzene → 1,2-Bis(2-ethylhexyl)benzene

HRID 868786

Reaction equation

[CH:1]1[C:6](Cl)=[CH:5][CH:4]=[C:3](Cl)[CH:2]=1.[CH2:9]([CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][Mg]Br)[CH3:10]>O>[CH2:9]([CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:12][CH:11]([CH2:9][CH3:10])[CH2:15][CH2:16][CH2:17][CH3:18])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A dry 1 L three-neck round bottom flask, equipped with a condenser and an addition funnel, was charged with Ni(dppp)2Cl2 (0.99 g, 1.83 mmol) and dichlorobenzene (26.7 g, 182 mmol). The reaction solution was cooled down to 0° C. and then (2-ethylhexyl)magnesium bromide solution (400 mmol) was added dropwise via the addition funnel under nitrogen. After addition was complete, the reaction was heated to reflux for 12 hours and then cooled down to room temperature. The reaction solution was poured into 100 mL of DI water. The mixture was extracted with MTBE (3×100 mL). The organic phase was combined, dried over anhydrous MgSO4, filtered and the solvent was removed by rotary evaporation. The mixture was purified by distillation under a reduced pressure to give the product (11.5 g, 21%) as colorless oil.

Workup

customA dry 1 L three-neck round bottom flask, equipped with a condenser and an addition funnel
additionAfter addition
temperaturethe reaction was heated
temperatureto reflux for 12 hours
temperaturecooled down to room temperature
extractionThe mixture was extracted with MTBE (3×100 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customthe solvent was removed by rotary evaporation
distillationThe mixture was purified by distillation under a reduced pressure

Sources & evidence

ORD record: ord-69a47141d8424544aa5db2c65d113327
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08968885B2

Linked notes

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