Toluene → HCID 59432159, compound

HRID 506480Notes

Reaction equation

HRID 506480 reaction equation
I(O)(=O)(=O)=O.[F:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([NH:13][CH:14]([CH2:17][OH:18])[CH:15]=[CH2:16])=[O:12])=[C:9]([C:21]([F:24])([F:23])[F:22])[CH:8]=1.C1(C)C=CC=CC=1.C(OCC)(=[O:34])C>C(#N)C.O>[F:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([NH:13][CH:14]([CH:15]=[CH2:16])[C:17]([OH:34])=[O:18])=[O:12])=[C:9]([C:21]([F:22])([F:23])[F:24])[CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 65185Metaperiodic acidHCID 59432164HCID 59432164, compound

Product 1

HCID 59432159HCID 59432159, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

At RT, 51.5 g (226 mmol) of periodic acid and 9.9 g (99 mmol) of CrO3 were dissolved in acetonitrile/water. Furthermore, 25 g (90.3 mmol) of 4-fluoro-N-(1-hydroxymethylallyl)-2-trifluoromethylbenzamide were dissolved in acetonitrile/water and the NalO4/CrO3 solution which had been prepared earlier was added dropwise at 0-5° C. over a period of 3 h. The mixture was then stirred at RT for 15 h. 400 ml of 6% strength Na2HPO4 solution were then added dropwise, toluene and ethyl acetate were added and the phases were separated. The aqueous phase was re-extracted with ethyl acetate. The combined organic phases were washed, dried and concentrated. This gave 24.1 g (92% of theory) of the title compound.

Workup

  1. customthe NalO4/CrO3 solution which had been prepared earlier
  2. additionwas added dropwise at 0-5° C. over a period of 3 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was re-extracted with ethyl acetate
  5. washThe combined organic phases were washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7e291798a00f4c9b9f345f588364d3d6
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

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