Sodium Carbonate → 5-(4-Tert-butylphenyl)furan-2-carbaldehyde

HRID 2197667

Reaction equation

HRID 2197667 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:12]([C:14]1[O:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.C(OCC)(=O)C.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>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:17]2[O:18][C:14]([CH:12]=[O:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 775951-Bromo-4-tert-butylbenzeneHCID 27343555-Formylfuran-2-boronic acid

Product 1

HCID 225667165-(4-Tert-butylphenyl)furan-2-carbaldehydeYield 72.2%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask containing 1-bromo-4-tert-butyl-benzene (1.5 g, 7.04 mmol) and 5-formyl-2-furan-boronic acid (1.47 g, 10.56 mmol) in dimethoxyethane (80 mL) and ethanol (20 mL) was added an aqueous solution of sodium carbonate (2.24 g, 21.12 mmol) m water (30 mL). The reaction mixture was stirred at room temperature for 5 minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (404 mg, 0.35 mmol). The reaction mixture was heated at 70° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (500 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated under vacuum. The crude product was purified by silica gel chromatography eluting with 20% ethyl acetate in hexanes to afford 5-(4-tert-butyl-phenyl)-furan-2-carbaldehyde (1.16 g, 72%) as a dark brown solid. 1H NMR (400 MHz, CDCl3): δ 1.35 (9H, s), 6.80 (1H, d, J=3.6 Hz), 7.31 (1H, d, J=3.6 Hz), 7.44-7.7.48 (2H, m), 7.74-7.77 (2H, m), 9.64 (1H, s); APCI-MS: 228.34.

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 1 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×150 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-03f78b92e0f1400d96206aa53f1d5bad
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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