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>[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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.04 mmol) (A.2.5.1) 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 concentrated in vacuo, redissolved in EtOAc and it was then washed twice with an aqueous solution of KHSO4, twice with a sat. aq. NaHCO3 solution and once with brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give the desired product as orange oil.
Workup
- concentrationThe mixture was concentrated in vacuo
- dissolutionredissolved in EtOAc
- washit was then washed twice with an aqueous solution of KHSO4, twice with a sat. aq. NaHCO3 solution and once with brine
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b10697d3bf5c418ea570b75eb4007615
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
Loading…