Triphenylphosphine → 3-Cyano-1-(3-bromoprop-2-en-1yl)benzene
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:20]Br.[C:22]([C:24]1[CH:25]=[C:26]([CH2:30][CH:31]=[CH:32]O)[CH:27]=[CH:28][CH:29]=1)#[N:23]>CC#N>[C:22]([C:24]1[CH:25]=[C:26]([CH2:30][CH:31]=[CH:32][Br:20])[CH:27]=[CH:28][CH:29]=1)#[N:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of Ph3P (1.0 g) in 40 mL of MeCN at 0° C. was added bromine (0.6 g) and the mixture was stirred at 0° C. for 15 minutes and then warmed to ambient temperature. To the suspension of Br2PPh3 was then added 3-cyano-1-(3-hydroxyprop-2-en-1yl)benzene (0.5 g) in 10 mL MeCN dropwise. The resulting solution was stirred at 60° C. for 30 minutes, cooled to ambient temperature and concentrated. The residue was triturated with 10% hexane in ethyl acetate. The mixture was filtered through a silica gel pad and the filtrate was concentrated to afford 0.71 g of 3-cyano-1-(3-bromoprop-2-en-1yl)benzene as a yellow oil.
Workup
- temperaturewarmed to ambient temperature
- stirringThe resulting solution was stirred at 60° C. for 30 minutes
- temperaturecooled to ambient temperature
- concentrationconcentrated
- customThe residue was triturated with 10% hexane in ethyl acetate
- filtrationThe mixture was filtered through a silica gel pad
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-6e11a0a16a4d469184a91ed06a213e0c
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350761B1
Reaction notes
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