Sodium Carbonate → HCID 86658337, compound

HRID 2198029Notes

Reaction equation

HRID 2198029 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:19]1[CH:20]=[C:21]([CH:24]=[O:25])[O:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:19]2[CH:20]=[C:21]([CH:24]=[O:25])[O:22][CH:23]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 86658337HCID 86658337, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3,5-bis(trifluoromethyl)phenylboronic acid (8.84 g), 4-bromo-2-furaldehyde (5.0 g), 2M aqueous sodium carbonate solution (71.4 mL), tetrakis(triphenylphosphine)palladium(0) (1.65 g) in 1,2-dimethoxyethane (300 ml) was stirred under an argon gas atmosphere at 90° C. for 16 hr. After cooling to room temperature, the reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate 98:2-90:10) to give the title compound (7.26 g, yield 82%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate 98:2-90:10)

Sources & evidence

ORD record
ord-a10ee9bc31994f468c94a92f35f727fd
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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