Dichloromethane → 6-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-bromoethoxy)benzoyl]benzo[b]thiophene

HRID 2198614Notes

Reaction equation

HRID 2198614 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.[CH3:14][S:15]([O:18][C:19]1[CH:20]=[CH:21][C:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([O:33][S:34]([CH3:37])(=[O:36])=[O:35])=[CH:29][CH:28]=3)[S:24][C:23]=2[CH:38]=1)(=[O:17])=[O:16].ClCCl.FC(F)(F)S(O)(=O)=O>C(Cl)(Cl)Cl>[CH3:14][S:15]([O:18][C:19]1[CH:20]=[CH:21][C:22]2[C:26]([C:9](=[O:11])[C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][Br:1])=[CH:13][CH:12]=3)=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([O:33][S:34]([CH3:37])(=[O:35])=[O:36])=[CH:31][CH:32]=3)[S:24][C:23]=2[CH:38]=1)(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62406Trifluoromethanesulfonic acidHCID 3506174-(2-Bromoethoxy)benzoic acidHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

Product 1

HCID 204790006-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-bromoethoxy)benzoyl]benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

One g. of 4-(2-bromoethoxy)benzoic acid was converted to the acid chloride, and was combined with 1.2 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, 20 ml. of dichloromethane and 0.5 ml. of trifluoromethanesulfonic acid. The mixture was stirred under reflux overnight, and was then poured into ice-water. The organic layer was separated, washed with sodium carbonate solution, dried and evaporated under vacuum to obtain 2.1 g. of brown oil. The oil was chromatographed over a 4×8 cm. silica gel column with 9/1 toluene/ethyl acetate and the product-containing fractions were combined and evaporated under vacuum to obtain 1.8 g. of purified product as an oil. The product was identified by its MH+ molecular ion, m/e 626, in the field desorption mass spectrum and by an absorption maximum in the infrared spectrum, in chloroform, at 1645 cm.-1 attributable to the CO function. A small sample was recrystallized from methanol to obtain white crystals, m.p. 105°-107°.

Workup

  1. temperatureunder reflux overnight
  2. customThe organic layer was separated
  3. washwashed with sodium carbonate solution
  4. customdried
  5. customevaporated under vacuum
  6. customto obtain 2.1 g
  7. customThe oil was chromatographed over a 4×8 cm
  8. customevaporated under vacuum
  9. customto obtain 1.8 g
  10. customA small sample was recrystallized from methanol
  11. customto obtain white crystals, m.p. 105°-107°

Sources & evidence

ORD record
ord-bfbf7298635249879a63ddea7acfde47
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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