5-Fluoro-1-benzofuran → 5-Fluoro-2,3-dihydrobenzofuran

HRID 1872841Notes

Reaction equation

HRID 1872841 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1>[Pd].C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 1

HCID 117883225-Fluoro-1-benzofuran

Product 1

HCID 223986405-Fluoro-2,3-dihydrobenzofuranYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5-fluorobenzofuran and 10% palladium on carbon in acetic acid (25 ml) was hydrogenated under 50 psi for 12 hours. The catalyst was filtered through celite and the celite was washed with methylene chloride (200 ml). The organic layer was washed with 1N NaOH (3×100 ml) and brine (3×100 ml) and dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afforded 2.59 g (85%) of product as a clear oil: 1H NMR (300 MHz, CDCl3): δ3.12 ppm (t, 2H, J=8.7 Hz), 4.58 (t, 2H, J=8.7 Hz), 6.68 (dd, 1H, J=8.7, 4.2 Hz), 6.79 (tm, 1H, J=8.7 Hz), 6.89 (dm, 1H, J=8.1 Hz).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. washthe celite was washed with methylene chloride (200 ml)
  3. washThe organic layer was washed with 1N NaOH (3×100 ml) and brine (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-82a0e8d731af4a7ea812707b7207a391
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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