Sodium Carbonate → HCID 2783407, compound

HRID 1391737Notes

Reaction equation

HRID 1391737 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[CH:5]=1)=[O:3].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 165023'-BromoacetophenoneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 2783407HCID 2783407, compoundYield 76.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-bromoacetophenone (661 μL, 5.00 mmol) and 4-(triflouromethyl)benzeneboronic acid (950 mg, 5.00 mmol) in DME (50 mL) was added Na2CO3 (1.32 g, 12.50 mmol) and Pd(PPh3)4 (283 mg, 0.24 mmol) and water (25 mL). The mixture was then stirred at 100° C. for 20 hours, diluted with water and extracted with EtOAc. The organic layer was then washed with brine, dried (Na2SO4), filtered and reduced. Purification by flash chromatography (silica) eluting with petrol:EtOAc (gradient 19:1 to 9:1) afforded the title compound (1.01 g).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was then washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customPurification by flash chromatography (silica)
  6. washeluting with petrol

Sources & evidence

ORD record
ord-7a2ffe94d4e84e36a1f881367b09f035
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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