HCID 629261, compound → HCID 14547484, compound

HRID 2232359Notes

Reaction equation

HRID 2232359 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11](Br)=[C:10](Br)[S:9][C:8]=2[CH:14]=1)(=[O:3])[CH3:2]>C(O)C.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[CH:10][S:9][C:8]=2[CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 629261HCID 629261, compound

Product 1

HCID 14547484HCID 14547484, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Acetyl-2,3-dibromobenzo[b]thiophene (6.68 g, 20 mmole) was dissolved in a mixture of ethanol and ethyl acetate (100 ml each) and MgO (1.6 g) and (20% Pd(OH2)/C (800 mg) were added under a N2 atmosphere. Hydrogenolysis was carried out at 40 psi of H2 at room temperature for 3 hours. The catalyst was removed by filtration and the solvent was removed in vacuo. The residue was partitioned between CHCl3 (100 ml) and H2O (50 ml). The CHCl3 layer was washed with H2O (50 ml). The aqueous layers were combined and back-extracted with CHCl3 (30 ml). The CHCl3 solutions were combined, dried over Na2SO4 and the solvent evaporated in vacuo to yield 3.8 g of product which was used in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between CHCl3 (100 ml) and H2O (50 ml)
  4. washThe CHCl3 layer was washed with H2O (50 ml)
  5. extractionback-extracted with CHCl3 (30 ml)
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-954673740796403cb13bb89db9062fee
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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