Hydrochloric Acid → HCID 58307068, compound

HRID 1909902Notes

Reaction equation

HRID 1909902 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C)=[C:4]([CH3:12])[C:3]=1[C:13]([F:16])([F:15])[F:14].C(O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:12])[C:3]=1[C:13]([F:14])([F:15])[F:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11430Potassium CarbonateHCID 58306937HCID 58306937, compound

Product 1

HCID 58307068HCID 58307068, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N-[4-bromo-2-methyl-3-(trifluoromethyl)phenyl]acetamide (9.0 g) and ethanol (40 mL) was added concentrated hydrochloric acid (40 mL) at room temperature. The reaction mixture was stirred at 100° C. for 4 hours. The reaction mixture was left to be cooled to room temperature, and ethyl acetate and water were added thereto, followed by alkalification with potassium carbonate. Then, a liquid-separation operation was carried out, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-60:40) to obtain 4-bromo-2-methyl-3-(trifluoromethyl) aniline (6.9 g).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-60:40)

Sources & evidence

ORD record
ord-ba80186f6a4545eea5ff4c9802fd3e43
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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