Hydrochloric Acid → HCID 18405168, compound

HRID 1017789Notes

Reaction equation

C([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([Br:14])=[CH:9][C:8]=1[CH3:15].C(#N)C(C)C.Cl.[O:22]1CCC[CH2:23]1>CCCCCC.C(OCC)C>[Br:14][C:10]1[C:11]([CH3:13])=[CH:12][C:7]([C:23]([CH:3]([CH3:2])[CH3:4])=[O:22])=[C:8]([CH3:15])[CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

31.2 ml of (50 mmol) of a 1.6 molar n-butyl lithium solution in hexane are added dropwise to a solution of 13.5 g (50 mmol) of 2,5-dibromo-p-xylene in 100 ml of tetrahydrofuran cooled to −78° C., the mixture is stirred for 30 minutes and then combined with 4.5 ml of (50 mmol) of isobutyronitrile. The reaction mixture is allowed to come back slowly to ambient temperature, stirred for 1 hour, then combined with 50 ml of 2N HCl and 70 ml of diethyl ether and stirred for another 16 hours. The aqueous phase is separated off and extracted 2× with diethyl ether. The combined organic phases are dried with Na2SO4, evaporated down and the residue is purified by flash chromatography (silica gel; petroleum ether to petroleum ether/ethyl acetate=9:1).

Workup

customto come back slowly to ambient temperature
stirringstirred for 1 hour
stirringstirred for another 16 hours
customThe aqueous phase is separated off
extractionextracted 2× with diethyl ether
dry with materialThe combined organic phases are dried with Na2SO4
customevaporated down
customthe residue is purified by flash chromatography (silica gel; petroleum ether to petroleum ether/ethyl acetate=9:1)

Sources & evidence

ORD record: ord-bba88c8153af44f09333d36f974894fe
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479524B1

Reaction notes

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