Trifluoroacetic anhydride → 4-chloro-2-fluoro-5-methyl-6-nitro-N-phenoxycarbonylaniline

HRID 1271753

Reaction equation

HRID 1271753 reaction equation
[Cl:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]([NH:6][C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[C:4]([F:19])[CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:33]([O-])([O-:35])=[O:34].[NH4+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[C:17]([CH3:18])=[C:16]([N+:33]([O-:35])=[O:34])[C:5]([NH:6][C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[C:4]([F:19])[CH:3]=1

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrate2×HCID 516892Sodium BicarbonateHCID 186156474-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

Product 1

HCID 186156464-chloro-2-fluoro-5-methyl-6-nitro-N-phenoxycarbonylanilineYield 103.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-Chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline (7.1 g, 25.4 mmol) was dissolved in chloroform (68 ml) and trifluoroaceticanhydride (13.5 ml) and ammonium nitrate (2.4 g, 30.5 mmol) were slowly added with stirring at ambient temperature. The stirring was continued for 18 hr when a second batch of ammonium nitrate (0.4 g, 5 mmol) was added and stirring continued for 8 hr. Water was added and solution was neutralized by slow addition of sodium bicarbonate solution followed by extration with chloroform. Oganic layer was dried and evaporated under reduced pressure to afford an oily product (8.5 g) which was used for the next step without purification.

Workup

  1. stirringstirring
  2. waitcontinued for 8 hr
  3. customOganic layer was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7f98b4c60eb14eb697a7a31a58b278a0
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Linked notes

Loading…