Toluene → HCID 117899706, compound

HRID 522436Notes

Reaction equation

HRID 522436 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=1B(O)O.C[N+]1([O-])CC[O:29]CC1.CCCCCC>C(OCC)(=O)C>[F:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=1[OH:29]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8058HexaneHCID 82029Methyl morpholine oxideHCID 22170959HCID 22170959, compound

Product 1

HCID 117899706HCID 117899706, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 300 ml of toluene were added 32.0 g (119 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl boronic acid produced by the method described in PCT International Publication No. WO 2007/034755 and 15.4 g (131 mmol) of N-methylmorpholine-N-oxide, followed by refluxing for 1 hour under heating. The reaction mixture was allowed to cool to room temperature. The solvent was distilled off under reduced pressure. The residue was subjected to extraction with ethyl acetate. The organic phase obtained was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=4:1), to obtain 25.5 g (yield: 89%) of an intended product.

Workup

  1. customproduced by the method
  2. temperatureby refluxing for 1 hour
  3. temperatureunder heating
  4. distillationThe solvent was distilled off under reduced pressure
  5. extractionThe residue was subjected to extraction with ethyl acetate
  6. customThe organic phase obtained
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-df32cfdc2c794093b8d1ba1edb63a8e8
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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