1,2-Dichloroethane → 1,1-Bis(4-dimethylaminophenyl)-2-bromopropene

HRID 1282456Notes

Reaction equation

[CH3:1][N:2]([CH3:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:10][CH3:11])=[CH:5][CH:4]=1.ClCCCl.[Br:26]Br.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:20][N:18]([CH3:19])[C:15]1[CH:14]=[CH:13][C:12]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:21])=[CH:8][CH:7]=2)=[C:10]([Br:26])[CH3:11])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a reactor were introduced 13.6 g (48.5 mmol) of the 1,1-bis(4-dimethylaminophenyl)propene and 54 mL of 1,2-dichloroethane under a nitrogen atmosphere. The contents were cooled to 0° C. Thereto was gradually added dropwise 7.76 g (48.5 mmol) of bromine. The resultant mixture was stirred at room temperature for 2.5 hours. Thereafter, 15.7 mL (194 mmol) of pyridine and 109 mL of toluene were added thereto and this mixture was stirred at 80° C. for 3 hours. After being cooled, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrate was purified by column chromatography and then crystallized from methanol to obtain 12.0 g (69%) of the target compound as green-yellow crystals.

Workup

temperatureAfter being cooled
washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
dry with materialsubsequently dried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate was purified by column chromatography
customcrystallized from methanol

Sources & evidence

ORD record: ord-291f11c9c412407dab8c973c1cd5e1ac
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455720B1

Reaction notes

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