1,2-Dimethoxyethane → HCID 117992110, compound

HRID 531006Notes

Reaction equation

HRID 531006 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([O:13][CH2:14][CH3:15])=[CH:11][C:10]([CH:16]=[O:17])=[CH:9][C:8]=1[CH:18]1[CH2:20][CH2:19]1)(=O)=O.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[F:30].[F-].[Cs+].COCCOC>O>[CH:18]1([C:8]2[CH:9]=[C:10]([CH:16]=[O:17])[CH:11]=[C:12]([O:13][CH2:14][CH3:15])[C:7]=2[C:27]2[CH:26]=[CH:25][C:24]([F:23])=[C:29]([F:30])[CH:28]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27343373,4-Difluorobenzeneboronic acidHCID 90423792HCID 90423792, compound

Product 1

HCID 117992110HCID 117992110, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1,1′-Bis(diphenylphosphino)ferrocene)dichloropalladium(II) (1.30 g) was added to a mixture of 2-cyclopropyl-6-ethoxy-4-formylphenyl trifluoromethanesulfonate (3.00 g), (3,4-difluorophenyl)boronic acid (5.60 g), cesium fluoride (5.39 g), and DME (15 mL), and the resultant mixture was stirred at 100° C. for 15 hours in an argon atmosphere. Water was added to the reaction mixture, and the mixture was filtered through celite. The filtrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.57 g).

Workup

  1. filtrationthe mixture was filtered through celite
  2. extractionThe filtrate was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a697681c21b48e38adcbacf1b6f327e
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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