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

HRID 1265376

Reaction equation

HRID 1265376 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 6212ChloroformSolvent

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 extraction with chloroform. Organic 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. extractionfollowed by extraction with chloroform
  4. customOrganic layer was dried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4741a347fe21462983bdea91d7fc2dad
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Linked notes

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