Allyl bromide → 2-(3,4-Dichlorophenyl)pent-4-enenitrile

HRID 1384967Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>C1CCCCC1.O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:16][CH:15]=[CH2:14])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3,4-dichlorophenylacetonitrile (800 g, 4.3 mol) in cyclohexane (16 l) at room temperature was carefully added aqueous sodium hydroxide solution (containing 1600 g of sodium hydroxide in 8 l of water). This addition caused an elevation of the reaction temperature to 50° C. Allyl bromide (572 g, 1.1 mol. equiv.) and tetra-n-butylammonium chloride hydrate (40 g, 0.03 mol. equiv.) were then added and the reaction stirred for one hour at 50° C. The aqueous phase was removed and the organic layer washed with water (10 l). The organic phase was filtered through silica gel (1 kg) under reduced pressure to give a yellow filtrate solution. The solvent was removed from the filtrate under reduced pressure to give the title compound as an oil (960 g) of 70% purity which was used without any further purification. TLC Rf=0.71 (silica, diethyl ether:hexane, 1:1, by volume). LRMS m/z=226 (m)+.

Workup

customat room temperature
additionThis addition
customto 50° C
customThe aqueous phase was removed
washthe organic layer washed with water (10 l)
filtrationThe organic phase was filtered through silica gel (1 kg) under reduced pressure
customto give a yellow filtrate solution
customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record: ord-ac9020bc04d645d2a48f6802ede6cd57
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262075B1

Reaction notes

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