Dimethylformamide → 2,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)benzenamine

HRID 463452Notes

Reaction equation

CN(C)C=O.Cl.[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([OH:15])=[C:10]([Cl:16])[CH:9]=1.[OH-].[K+].[F:19][C:20]([F:24])=[C:21]([F:23])[F:22]>O>[Cl:14][C:13]1[CH:12]=[C:11]([O:15][C:21]([F:23])([F:22])[CH:20]([F:24])[F:19])[C:10]([Cl:16])=[CH:9][C:8]=1[NH2:7]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 100 ml dimethylformamide (DMF), 75 g (0.035 mole) 4-amino-2,5-dichlorophenol, hydrochloride, and 3.0 g (0.05 mole) KOH (pellets ground to powder) was placed in a 500 ml 3-necked round bottom flask fitted with a mechanical stirrer, thermometer and reflux condenser and was stirred for about 1 hour. It was then heated to 85° C. with stirring and 6.0 g (0.06 mole) of tetrafluoroethylene was bubbled in while heating at 85°-90° C. The addition took about 10 minutes. The reactor and contents were cooled in an ice water bath and 200 ml of water were added. The product was extracted with 200 ml methylene chloride and then again with 100 ml methylene chloride. The extracts were combined and the solvents removed by vacuum distillation. A residue (7 g) remained.

Workup

customwas placed in a 500 ml 3-necked round bottom flask
customfitted with a mechanical stirrer
temperaturethermometer and reflux condenser
stirringwith stirring
temperaturewhile heating at 85°-90° C
additionThe addition
waittook about 10 minutes
temperatureThe reactor and contents were cooled in an ice water bath
extractionThe product was extracted with 200 ml methylene chloride
customthe solvents removed by vacuum distillation

Sources & evidence

ORD record: ord-987540b5256b4e5b9ac74ffb1b84ae6a
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04518804

Reaction notes

Loading…