Acetic Anhydride → HCID 600381, compound

HRID 1384839Notes

Reaction equation

HRID 1384839 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH3:11][C:12](OC(C)=O)=[O:13]>>[C:12]([C:8]1[C:4]2[CH:3]=[C:2]([CH3:1])[CH:10]=[CH:9][C:5]=2[S:6][CH:7]=1)(=[O:13])[CH3:11]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 843465-Methylbenzo(b)thiophene

Product 1

HCID 600381HCID 600381, compoundYield 50%

Procedure

1 g of 5-methylbenzo(b)thiophene (6.75×10−3 moles) was stirred at 55° C. with 0.8 ml of Ac2O (8.10×10−3 moles). 0.83 ml of BF3 Et2O were added and stirring was continued for 8 hours.11 The solvent was removed in the rotary evaporator and the residue was extracted with AcOEt and H2O. It was decanted and washed with NaHCO3 and H2O. It was dried with Na2SO4, the solvent was removed and the product was purified in successive columns of AcOEt/hexane (1:1) and toluene respectively. A product was obtained which was a mixture of the substitution isomers in positions 2- and 3- of the benzo(b)thiophene ring in a proportion of approximately 20/80 (determined by the ratios of the areas of the NMR signals), which was passed to the following reaction. Yield: 50%.

Workup

  1. custom11 The solvent was removed in the rotary evaporator
  2. extractionthe residue was extracted with AcOEt and H2O
  3. customIt was decanted
  4. washwashed with NaHCO3 and H2O
  5. dry with materialIt was dried with Na2SO4
  6. customthe solvent was removed
  7. customthe product was purified in successive columns of AcOEt/hexane (1:1) and toluene respectively
  8. customA product was obtained which
  9. additiona mixture of the substitution isomers in positions 2-
  10. customwas passed to the following reaction

Sources & evidence

ORD record
ord-fc4be5a7cd23479281ebd7231ff7602b
Source dataset
uspto-grants-2001_07
Patent number
US06262056B1

Reaction notes

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