Sodium Methoxide → 2,4-Dichloro-6-(methoxymethyl)benzonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:4]=1[C:5]#[N:6].[CH3:13][O-:14].[Na+]>CO.CCOC(C)=O>[Cl:12][C:7]1[CH:8]=[C:9]([Cl:11])[CH:10]=[C:3]([CH2:2][O:14][CH3:13])[C:4]=1[C:5]#[N:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.04 mmol) (A.2.2.1.) in 2.5 mL MeOH was added a solution of NaOMe (1.27 mmol, 0.5M in MeOH). The reaction mixture was heated to 50° C. for 1 h. The mixture was conc. in vacuo, redissolved in EtOAc and it was then washed twice with an aq. soln. of KHSO4, twice with a sat. aq. NaHCO3 soln. and once with brine. The org. layer was dried over MgSO4 and conc. in vacuo to give the desired product as orange oil.
Workup
- washit was then washed twice with an aq. soln
- dry with materiallayer was dried over MgSO4 and conc. in vacuo
Sources & evidence
- ORD record
- ord-45ac1aaa117e4923b8a9f26fa20c01f3
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388197B2
Reaction notes
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