1,2-Dibromoethane → HCID 23130675, compound

HRID 2080030Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH3:12])=[C:5]([CH3:13])[CH:4]=1.BrCCBr.[N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH:28]=[O:29])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:28]([C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[N:18]=[CH:19][CH:20]=[CH:21]3)[OH:29])=[CH:4][C:5]=1[CH3:13])[CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Magnesium (83 mg, 3.40 mmol), 4-bromo-1-butyl-2-methylbenzene (722 mg, 3.18 mmol) and, as an initiator, catalytic amount of 1,2-dibromoethane were added to tetrahydrofuran (2.5 mL) under nitrogen atmosphere, and the mixture was stirred for 10 minutes under reflux. This mixture was cooled to 0° C., a solution of quinoline-6-carbaldehyde (100 mg, 6.36 mmol) in tetrahydrofuran (12 mL) was added thereto, followed by stirring for 1 hour at this temperature. An aqueous solution of saturated ammonium chloride was added to the reaction mixture, which was extracted with chloroform and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and the title compound (152 mg, 78%) was obtained as a yellow solid.

Workup

temperatureunder reflux
stirringby stirring for 1 hour at this temperature
extractionwas extracted with chloroform
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-166db18fc0fe44aa8175abee3a47fa52
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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