Triphenylphosphine → 3-Cyano-6-((4-methoxybenzyl)oxy)-1-(3-bromoprop-2-en-1-yl)benzene

HRID 1700288Notes

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]([CH2:40][CH:41]=[CH:42]O)[C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:28][CH:29]=1)#[N:23]>CC#N>[C:22]([C:24]1[CH:25]=[C:26]([CH2:40][CH:41]=[CH:42][Br:20])[C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:28][CH:29]=1)#[N:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of Ph3P (2.4 g) in 30 mL of MeCN at 0° C. was added bromine (1.5 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-6-((4-methoxybenzyl)oxy)-1-(3-hydroxyprop-2-en-1-yl)benzene (2.3 g) in 20 mL MeCN drop-wise. The resulting solution was stirred at ambient temperature for 1 hour, cooled to ambient temperature and concentrated. The residue was purified on silica gel column (ethyl acetate/hexane, 1:9) to afford 3-cyano-6-((4-methoxybenzyl)oxy)-1-(3-bromoprop-2-en-1-yl)benzene (0.81 g) as a yellow oil.

Workup

temperaturewarmed to ambient temperature
stirringThe resulting solution was stirred at ambient temperature for 1 hour
temperaturecooled to ambient temperature
concentrationconcentrated
customThe residue was purified on silica gel column (ethyl acetate/hexane, 1:9)

Sources & evidence

ORD record: ord-c8e0a90305fd497f983a5ab08b563d28
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350761B1

Reaction notes

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