5-Fluoro-1-benzofuran → 5-Fluoro-2,3-dihydrobenzofuran
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered through celite
- washthe celite was washed with methylene chloride (200 ml)
- washThe organic layer was washed with 1N NaOH (3×100 ml) and brine (3×100 ml)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- 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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