Sodium Hydroxide → HCID 19779367, compound

HRID 1461731Notes

Reaction equation

HRID 1461731 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([N+:12]([O-])=O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+]>Cl>[NH2:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[F:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27365653-Chloro-4-fluoro-5-nitrobenzotrifluoride

Product 1

HCID 19779367HCID 19779367, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Chloro-4-fluoro-3-nitrotrifluoromethylbenzene (50 g) was added to a cooled (5° C.) solution of stannous chloride (140 g) in concentrated agueous hydrochloric acid (187 ml). After stirring for several hours at the ambient temperature (ca 22° C.), the reaction mixture was stood overnight. After basification by the addition of sodium hydroxide, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried, and the solvent removed by evaporation under reduced pressure. The residual yellow oil was kugelrohr distilled under reduced pressure to give 3-amino-5-chloro-4-fluorotrifluoromethylbenzene (32 g):bp. 105° C./11 mm Hg; 'H NMR δ (CDCl3) 7.03 (1H, dq), 6.90 (1H, dq).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent removed by evaporation under reduced pressure
  5. distillationThe residual yellow oil was kugelrohr distilled under reduced pressure

Sources & evidence

ORD record
ord-775e46c1ff9f4791ae7747f812f3f436
Source dataset
uspto-grants-1991_12
Patent number
US05077297

Reaction notes

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