Potassium Carbonate → HCID 21936374, compound

HRID 1669225Notes

Reaction equation

HRID 1669225 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[C:17]([F:23])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>O1CCOCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:17]1[CH:16]=[C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 21936374HCID 21936374, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To an ambient temperature solution of 4-(trifluoromethyl)phenylboronic acid (5.05 g, 26.59 mmol) in dioxane/water (15/15 mL) is added 4-bromo-2-fluoro-benzaldehyde (4.91 g, 24.17 mmol), tetrabutylammonium bromide (7.79 g, 24.17 mmol, potassium carbonate (9.18 g, 66.48 mmol) and is degassed for 10 min. Palladium(II) acetate (895 mg, 1.33 mmol) is added and the reaction mixture is heated to 70° C. After 2 h TLC (20% EtOAc/hexane) indicates complete consumption of starting material. The reaction is cooled to room temperature diluted with water and extracted with EtOAc (3×200 mL). The combined organic extracts are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (330 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (5.57 g, 86%). 1NMR (400 MHz, CDCl3) δ ppm: 10.41 (s, 1H), 7.98 (t, 1H, J=7.5 Hz), 7.74 (q, 4H, J=7.8 Hz), 7.52 (d, 1H, J=7.9 Hz), 7.41 (dd, 1H, J=11.2, 1.2 Hz).

Workup

  1. customis degassed for 10 min
  2. customconsumption of starting material
  3. temperatureThe reaction is cooled to room temperature
  4. additiondiluted with water
  5. extractionextracted with EtOAc (3×200 mL)
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed (330 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-39d6859a086143cfa1d6ad8cdc258bb4
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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