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Sodium Hydroxide → HCID 19779367, compound

HRID 1031121
Notes
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Reaction equation

HRID 1031121 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

HCID 19779367HCID 19779367, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
22 °C

Procedure

5-Chloro-4-fluoro-3-nitro-trifluoromethylbenzene (50g) was added to a cooled (5° C.) solution of stannous chloride (140g) in concentrated aqueous hydrochloric acid (187ml). After stirring for several hours at the ambient temperature (about 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-fluoro-trifluoromethylbenzene (32g): boiling point 105° C./11 mm Hg;

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-7347b290abf94bfab7e7648098413c36
Source dataset
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05109004

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes