Water → 2-Bromo-5-ethanesulfonyl-thiophene

HRID 646411Notes

Reaction equation

HRID 646411 reaction equation
[CH2:1]1COC[CH2:2]1.CO.[Br:8][C:9]1[S:10][C:11](SCC)=[CH:12][CH:13]=1.O.O[O:19][S:20]([O-:22])=O.[K+]>C(Cl)Cl>[Br:8][C:9]1[S:10][C:11]([S:20]([CH2:1][CH3:2])(=[O:22])=[O:19])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21899815MeOH tetrahydrofuranHCID 220320792-Bromo-5-(ethylthio)thiopheneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 592646582-Bromo-5-ethanesulfonyl-thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL THF/MeOH (2:1) solution of 2-Bromo-5-ethylsulfanyl-thiophene (CAS 19991-60-7) is stirred at 0-10° C. while 8 mL H2O, then 3 equivalents of Oxone are added. The reaction mixture is stirred three hours at room temperature, then is diluted with CH2Cl2, filtered, washed with aq. NaHCO3 and brine, dried (Na2SO4) and concentrated in vacuo. The crude mixture is purified by silica gel column chromatography (gradient: 0-20% EtOAc/CH2Cl2) to give title intermediate that is confirmed by NMR.

Workup

  1. filtrationfiltered
  2. washwashed with aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture is purified by silica gel column chromatography (gradient: 0-20% EtOAc/CH2Cl2)
  6. customto give title intermediate that

Sources & evidence

ORD record
ord-d1cabdcb221448c2bb76422091dc66d2
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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