5-Chloro-1-benzofuran → 5-Chloro-2,3-dihydro-1-benzofuran

HRID 257515

Reaction equation

HRID 257515 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1>CCO.[Rh]>[Cl: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 900135-Chloro-1-benzofuran

Product 1

HCID 5929645-Chloro-2,3-dihydro-1-benzofuranYield 91%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

5-Chloro-benzofurane (2 g, 13.11 mmol) in dry EtOH (20 ml) was hydrogenated over 10% Rh/C (251 mg) catalyst at room temperature under atmospheric pressure. When H2 absorption ceased the catalyst was filtered off and the filtrate was concentrated in vacuo to give 1.84 g (91%) of (33) as a colourless solid. 1H-NMR (80 MHz, CDCl3) δ 7.00 (d, 2H, J=8.53 Hz), 6.62 (d, 1H, J=8.53), 4.5 (t, 2H), 3.11 (t, 2H).

Workup

  1. customWhen H2 absorption
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-479282472fb84b2692964152d1140bd8
Source dataset
uspto-grants-1993_11
Patent number
US05262430

Linked notes

Loading…