Triphenylethylene → 1-Bromo-1,2,2-triphenylethene
Reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21]Br>ClCCCl>[Br:21][C:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[C:7]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Into a reactor were introduced 12.5 g (48.8 mmol) of the 1,1,2-triphenylethylene and 50 mL of 1,2-dichloroethane under a nitrogen atmosphere. The contents were cooled to 0° C., and 7.80 g (48.8 mmol) of bromine was gradually added dropwise thereto. This mixture was stirred at room temperature for 1 hour. The resultant reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, saturated aqueous sodium thiosulfate solution, and saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The resultant concentrate was recrystallized from ethanol and ethyl acetate to obtain 11.3 g (69%) of the target compound as white crystals.
Workup
- customThe resultant reaction mixture
- washwas washed with saturated aqueous sodium hydrogen carbonate solution, saturated aqueous sodium thiosulfate solution, and saturated aqueous sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- customThereafter, the solvent was removed under reduced pressure
- concentrationThe resultant concentrate
- customwas recrystallized from ethanol and ethyl acetate
Sources & evidence
- ORD record
- ord-cc48a919e86347428772c38c7d6007d9
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455720B1
Reaction notes
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