Toluene → HCID 117899776, compound

HRID 522452Notes

Reaction equation

HRID 522452 reaction equation
C1(C)C=CC=CC=1.[CH3:8][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]=1B1OC(C)(C)C(C)(C)O1.C[N+]1([O-])CC[O:35]CC1.CCCCCC>C(OCC)(=O)C>[CH3:8][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:35]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8058HexaneHCID 82029Methyl morpholine oxideHCID 123296293HCID 123296293, compound

Product 1

HCID 117899776HCID 117899776, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 200 ml of toluene were added 20.24 g (58.5 mmol) of [2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (a compound described in PCT International Publication No. WO 2012/176856 as Compound No. 55-47) and 8.22 g (70.16 mmol) of N-methylmorpholine-N-oxide. The mixture was refluxed for 2 hours under heating. The reaction mixture was allowed to cool to room temperature, washed and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 10.54 g (yield: 76%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureunder heating
  3. washwashed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-6ffb426d1ddf47a2b143e9a79d506b7b
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

Loading…