Acetic Acid → HCID 58306937, compound

HRID 1909898Notes

Reaction equation

HRID 1909898 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:15])[CH3:14].C(O)(=O)C.[Br:20]Br.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Br:20][C:6]1[CH:5]=[CH:4][C:3]([NH:12][C:13](=[O:15])[CH3:14])=[C:2]([CH3:1])[C:7]=1[C:8]([F:10])([F:11])[F:9]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 11430Potassium CarbonateHCID 24408Bromine5×HCID 66867834HCID 66867834, compound

Product 1

HCID 58306937HCID 58306937, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-[2-methyl-3-(trifluoromethyl)phenyl]acetamide (6.2 g) and acetic acid (40 ml) was added an acetic acid solution (10 ml) of bromine (1.8 ml) under water-cooling. The reaction liquid was stirred at room temperature overnight and then at 50° C. for 2 hours. In addition, to the reaction liquid was added bromine (1.5 ml) under water-cooling, followed by stirring at 50° C. for 1 day. In addition, to the reaction liquid was added bromine (2.0 ml) under water-cooling, followed by stirring at 50° C. for 1 day. In addition, to the reaction liquid was added bromine (2.0 ml) under water-cooling, followed by stirring at 50° C. for 1 day. In addition, to the reaction liquid was added bromine (2.0 ml) under water-cooling, followed by stirring at 50° C. for 4 days. The reaction liquid was poured into ice water (about 200 g), ethyl acetate was added thereto, followed by neutralization with potassium carbonate. A liquid-separation operation was carried out, and the organic layer was washed with an aqueous sodium thiosulfate solution and saturated brine in this order, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to obtain N-[4-bromo-2-methyl-3-(trifluoromethyl)phenyl]acetamide (9.0 g).

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. waitat 50° C. for 2 hours
  4. customIn addition, to the reaction liquid
  5. temperaturecooling
  6. stirringby stirring at 50° C. for 1 day
  7. customIn addition, to the reaction liquid
  8. temperaturecooling
  9. stirringby stirring at 50° C. for 1 day
  10. customIn addition, to the reaction liquid
  11. temperaturecooling
  12. stirringby stirring at 50° C. for 1 day
  13. customIn addition, to the reaction liquid
  14. temperaturecooling
  15. stirringby stirring at 50° C. for 4 days
  16. customThe reaction liquid
  17. additionwas added
  18. washthe organic layer was washed with an aqueous sodium thiosulfate solution and saturated brine in this order
  19. dry with materialdried over anhydrous sodium sulfate
  20. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a42665e662f0410c8b12f68337b620dd
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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