Di-tert-butyl dicarbonate → 4-Fluoro-3-(furan-2-yl)benzaldehyde

HRID 478286Notes

Reaction equation

HRID 478286 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].C([Sn](CCCC)(CCCC)[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)CCC.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C=O)C.C(OCC)(=O)C.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:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 234975044-Fluoro-3-(furan-2-yl)benzaldehydeYield 480.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

3-Bromo-4-fluorobenzaldehyde (1 g, 4.93 mmol) in DMF (25 ml) was treated with 2-(tributylstannyl)furan (2.4 ml, 1.05 mmol), di-tert-butyl dicarbonate (1.75 g, 4.94 mmol), and tetrakis(triphenylphosphine)palladium (0) (570 mg, 0.4 mmol). The mixture was heated at 110° C. in a sealed high pressure tube over night, allowed to cool to ambient temperature, diluted with ethyl acetate, and washed with brine. The organic layer was further washed with 1N HCl, saturated NaHCO3, brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography using hexanes:diethyl ether (20:1) as eluent to provide the title compound as a pale yellow oil (0.96 g, 98%).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with brine
  3. washThe organic layer was further washed with 1N HCl, saturated NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ca6f43ea12b14d00a0c0d17d97342fd2
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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