Boron trifluoride etherate → HCID 67069101, compound

HRID 909787Notes

Reaction equation

HRID 909787 reaction equation
[SiH](CC)(CC)CC.B(F)(F)F.CCOCC.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:37])=[C:22]([C:24]([C:26]2[CH:31]=[C:30]([F:32])[C:29]([O:33][CH2:34][CH3:35])=[CH:28][C:27]=2[F:36])=O)[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(#N)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:37])=[C:22]([CH2:24][C:26]2[CH:31]=[C:30]([F:32])[C:29]([O:33][CH2:34][CH3:35])=[CH:28][C:27]=2[F:36])[CH:23]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 67069095HCID 67069095, compound

Product 1

HCID 67069101HCID 67069101, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Procedure

Then, Et3SiH (5.93 mL, 0.0371 mol) and BF3.Et2O (2.83 mL, 0.0224 mol) were added sequentially to a chloroform-acetonitrile (1:1; 60 mL) solution of (5-bromo-2-chlorophenyl)(4-ethoxy-2,5-difluorophenyl)methanone (5.58 g, 0.0149 mol) at 4° C. The reaction mixture was warmed to room temperature, stirred for 12 hours and stirred at 45° C. for further three hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a colorless oily title compound (3.8 g, 71%).

Workup

  1. stirringstirred at 45° C. for further three hours
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained
  7. customby evaporating the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9a9df114cf4d4c4095b044d3103dbd24
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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