Sodium Carbonate → 5-[3,5-bis(trifluoromethyl)phenyl]furan-2-carbaldehyde

HRID 2198058Notes

Reaction equation

HRID 2198058 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:25])([F:24])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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:9][C:10]([F:24])([F:25])[C:11]1[CH:12]=[C:13]([C:2]2[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 7372105-[3,5-bis(trifluoromethyl)phenyl]furan-2-carbaldehydeYield 99.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromofuran-2-carbaldehyde (2.54 g, 14.5 mmol), [3,5-bis(trifluoromethyl)phenyl]boronic acid (3.93 g, 15.2 mmol), tetrakis(triphenylphosphine)palladium (0.59 g, 0.51 mmol) and 2M sodium carbonate solution (36 mL, 72 mmol) in THF (150 ml) was stirred under an argon atmosphere for 16 hr. The reaction solution was allowed to cool to room temperature and concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate filtration, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate), and the obtained solid was disrupted in hexane to give the title compound (4.46 g, yield>99%) as a pale-yellow solid. LC/MS (ESI+) m/z: 309 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate filtration
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3d73456eca224bb2aeb6968a57610dce
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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