4-Bromophenol → 2-(4-bromophenoxy)acetonitrile
Reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.Br[CH2:10][C:11]#[N:12].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:10][C:11]#[N:12])=[CH:1][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of p-bromophenol (2.61 g; 15.1 mmol), bromoacetonitrile (1.11 mL; 15.9 mmol), and Cs2CO3 (7.40 g; 22.7 mmol) in anhyd MeCN (25 mL) was heated at 80° C., under N2 overnight. The mixture was cooled, filtered through a pad of Celite and concentrated in vacuo. The residue was dissolved in a minimal amount of EtOAc/hexanes and filtered through a short pad of silica gel (EtOAc/hexanes eluent), affording the title compound as a colorless, waxy solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.75 (s, 2H), 6.88 (m, 2H), 7.46 (m, 2H).
Workup
- temperatureThe mixture was cooled
- filtrationfiltered through a pad of Celite
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in a minimal amount of EtOAc/hexanes
- filtrationfiltered through a short pad of silica gel (EtOAc/hexanes eluent)
Sources & evidence
- ORD record
- ord-2e3dec706c6140d2ab3636bcf2ad8c27
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822518B2
Reaction notes
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