Hydrochloric Acid → HCID 23358997, compound

HRID 232664Notes

Reaction equation

HRID 232664 reaction equation
S(=O)(=O)(O)O.N([O-])=O.[Na+].[F:10][C:11]1[C:17]([F:18])=[C:16]([CH3:19])[C:15]([F:20])=[CH:14][C:12]=1N.[ClH:21]>C(O)(=O)C.[Cu]Cl>[F:18][C:17]1[C:11]([F:10])=[C:12]([Cl:21])[CH:14]=[C:15]([F:20])[C:16]=1[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 184250192,3,5-Trifluoro-4-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 23358997HCID 23358997, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To conc. sulfuric acid (3 ml) is added sodium nitrite (0.3 g). The mixture is stirred at 70° C. for 10 minutes and then cooled to below 40° C. and thereto a solution of 2,3,5-trifluoro-4-methylaniline (0.48 g) in acetic acid (5 ml) is added dropwise below 40° C. After stirring for 30 minutes, the reaction mixture is added dropwise to a solution of copper (I) chloride (1.04 g) in conc. hydrochloric acid (10.4 ml) and the mixture is stirred at 80° C. for 30 minutes and then cooled. The resultant mixture is poured into ice-water, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and purified by silica-gel column-chromatography (eluent; dichloromethane: n-hexane=1:4) to give 2,3,6-trifluoro-4-chlorotoluene (0.22 g).

Workup

  1. temperaturecooled to below 40° C.
  2. stirringAfter stirring for 30 minutes
  3. stirringthe mixture is stirred at 80° C. for 30 minutes
  4. temperaturecooled
  5. extractionextracted with dichloromethane
  6. washthe extract is washed with water
  7. customdried
  8. distillationThe solvent is distilled off under reduced pressure
  9. custompurified by silica-gel column-chromatography (eluent; dichloromethane: n-hexane=1:4)

Sources & evidence

ORD record
ord-9eea9288c44845239e59941f5d1a9cf0
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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