p-Toluenesulfonic acid → HCID 178432087, compound

HRID 926487Notes

Reaction equation

HRID 926487 reaction equation
O=[C:2]([CH3:20])[CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:4]([O:6]CC)=O.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br:21][C:22]1[CH:23]=[C:24]2[C:25](=[CH:27][CH:28]=1)[N:26]=[C:2]([CH3:20])[C:3]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)=[C:4]2[OH:6]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7583Diphenyl EtherHCID 78074-BromoanilineHCID 86715644HCID 86715644, compound

Product 1

HCID 178432087HCID 178432087, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A round-bottomed flask equipped with a Dean-Stark apparatus was charged with ethyl 3-oxo-2-(4-(trifluoromethyl)benzyl)butanoate (7.00 g, 24.3 mmol, Intermediate 26: step a), 4-bromoaniline (4.20 g, 24.2 mmol), para-toluenesulfonic acid (0.418 g, 2.4 mmol), and toluene (121 mL). The mixture was heated to 125° C. After 16 hours, the flask was cooled to room temperature. The toluene was removed by rotary evaporation to provide an orange colored solid. A mixture of the solid and diphenyl ether (48.4 mL) was heated to 220° C. After 60 minutes, the mixture was cooled to room temperature at which point a yellow solid crashed out of solution. Hexanes (150 mL) were added. The mixture was filtered through filter paper, rinsing with hexanes. The yellow solids were collected, dried, and then used in the next step without further purification.

Workup

  1. customA round-bottomed flask equipped with a Dean-Stark apparatus
  2. temperaturethe flask was cooled to room temperature
  3. customThe toluene was removed by rotary evaporation
  4. customto provide an orange colored solid
  5. temperaturewas heated to 220° C
  6. waitAfter 60 minutes
  7. temperaturethe mixture was cooled to room temperature at which point a yellow solid
  8. filtrationThe mixture was filtered
  9. filtrationthrough filter paper
  10. washrinsing with hexanes
  11. customThe yellow solids were collected
  12. customdried
  13. customused in the next step without further purification

Sources & evidence

ORD record
ord-bcdd5616e0e74e69b3a319917c0fd404
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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