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

HRID 992041Notes

Reaction equation

HRID 992041 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 sequentially with 1N NaOH (3×100 ml), 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): δ 3.12 (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 sequentially with 1N NaOH (3×100 ml), 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-a77dfad18ea649c5a52a59569e47a964
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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