Dimethylformamide → 2,6-Dichloro-4-[2-(2-naphthalenyloxy)ethoxy]benzonitrile
Reaction equation
Br[C:2]1[C:21]([Cl:22])=[CH:20][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[CH:4][C:3]=1[Cl:23].[CH3:24][N:25](C)C=O>[C-]#N.[Na+]>[Cl:23][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[CH:20]=[C:21]([Cl:22])[C:2]=1[C:24]#[N:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 155 °C
Procedure
A mixture of 2-[2-(4-bromo-3,5-dichlorophenoxy)ethoxy]naphthalene (3.28 g) in dimethylformamide (10 mL) and cuprous cyanide (0.833 g) was heated under argon at 155° C. for four hours. The cooled mixture was diluted with aqueous 10% sodium cyanide solution (100 mL) and extracted twice with dichloromethane. The organic solutions were washed in turn with aqueous 10% sodium cyanide solution and water, dried (Na2SO4), filtered and evaporated to give 2.2 g of crude 2,6-dichloro-4-[2-(2-naphthalenyloxy)ethoxy]benzonitrile. A portion crystallized from dichloromethanediethyl ether provide pure colorless material, mp 156°-158° C.
Workup
- extractionextracted twice with dichloromethane
- washThe organic solutions were washed in turn with aqueous 10% sodium cyanide solution and water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-934396e911484d1f950057e522f7722a
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
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