Hydrochloric Acid → 5-Bromo-2,4-difluoro-3-methylbenzenamine
Reaction equation
Cl.C(O)C.[Br:5][C:6]1[C:7]([F:17])=[C:8]([CH3:16])[C:9]([F:15])=[C:10]([N+:12]([O-])=O)[CH:11]=1>O.[Fe]>[Br:5][C:6]1[C:7]([F:17])=[C:8]([CH3:16])[C:9]([F:15])=[C:10]([CH:11]=1)[NH2:12]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of iron powder (26.6 g, 100 mesh) in water (60 ml), with vigorous stirring at 50° C., was slowly added concentrated hydrochloric acid (4 ml). After hot ethanol (120 ml) was mixed, 3-bromo-2,6-difluoro-5-nitrotoluene (40 g) was added dropwise to the suspension at 75° to 78° C. during 30 minutes. The reacting mixture was refluxed for 1 hour, insoluble materials were filtered off through Celite pad, and then the materials were washed with hot ethanol. To the filtrate and washings were added ice water (400 ml) and the resulting precipitate was recrystallized from hexane to give the title compound (18.66 g) as pale brown needles, mp 68°-68.5° C.
Workup
- temperatureThe reacting mixture was refluxed for 1 hour
- filtrationinsoluble materials were filtered off through Celite pad
- washthe materials were washed with hot ethanol
- additionTo the filtrate and washings were added ice water (400 ml)
- customthe resulting precipitate was recrystallized from hexane
Sources & evidence
- ORD record
- ord-f454ab7016aa4d6e9135c2b034fecafb
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04894458
Reaction notes
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