Water → 2-(3,4-Dichlorophenoxy)-5-nitrobenzonitrile

HRID 1155731Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].Cl[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 91.3 grams (g) (0.56 moles) of 3,4-dichlorophenol dissolved in 500 milliliters (ml) of dimethyl sulfoxide (DMSO) was added 22.4 g (0.56 moles) of sodium hydroxide (NaOH). The slurry was heated at 60° C. for 15 minutes and 100 g (0.55 moles) of 2-chloro-5-nitrobenzonitrile was added. The mixture was heated at 75° C. for 3 hours (hrs). The reaction mixture was cooled and poured into a slurry of 200 ml of 2 normal (2 N) NaOH and 1800 ml of ice and water with the product precipitating. The product was collected by filtration, washed well with water and dried, to obtain 163.3 g of product (96.4% yield), mp 154°-155° C. Recrystallization from 3-methoxy-2-propanol (Dowanol® PM The Dow Chemical Company, Midland, Michigan) afforded purified 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile, melting at a melting point (mp) of 155°-156° C. The prominent infrared bands for 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile were as follows: IR (Nujol) 2250, 1620, 1580, 1520, 1465, 1360, 1270, 1130, 1040 and 895 cm-1.

Workup

temperatureThe mixture was heated at 75° C. for 3 hours (hrs)
temperatureThe reaction mixture was cooled
customprecipitating
filtrationThe product was collected by filtration
washwashed well with water
customdried

Sources & evidence

ORD record: ord-a0d08859422e4b6a9eefd2830a1ee891
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04332820

Reaction notes

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