1,1-Dichloroethane → Acetic acid, 2-[(3-bromophenyl)sulfonyl]-, methyl ester

HRID 602795Notes

Reaction equation

HRID 602795 reaction equation
COC(=O)CS[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1.ClC1C=CC=[C:17]([C:21]([O:23]O)=[O:22])C=1.[S:25]([O-:29])([O-])(=[O:27])=S.[Na+].[Na+].Cl[CH:33](Cl)C>>[CH3:33][O:23][C:21](=[O:22])[CH2:17][S:25]([C:10]1[CH:11]=[CH:6][CH:7]=[C:8]([Br:12])[CH:9]=1)(=[O:29])=[O:27]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 62804946HCID 62804946, compound

Product 1

HCID 60768756Acetic acid, 2-[(3-bromophenyl)sulfonyl]-, methyl esterYield 93%

Procedure

A solution of 6.0 g (23 mmol) of (3-bromo-phenylsulfanyl)-acetic acid methyl ester in 50 mL of dichloroethane was treated with 6.2 g (25 mmol) of 3-chloroperbenzoic acid. After 30 min of stirring another 6.2 g (25 mmol) of 3-chloroperbenzoic acid were added, the resulting suspension was stirred overnight at RT and then treated with a 0.5 M aqueous solution of sodium thiosulfate. The phases were separated and the aqueous one extracted twice with diethylether. The combined organic phases were washed with a ca. 1M aqueous NaHCO3 solution, dried over Na2SO4, filtered and evaporated to give 6.3 g (93%) of (3-bromo-benzenesulfonyl)-acetic acid methyl ester as a colorless oil, MS: 312 (MNH4+, 1Br).

Workup

  1. additionwere added
  2. customThe phases were separated
  3. extractionthe aqueous one extracted twice with diethylether
  4. washThe combined organic phases were washed with a ca. 1M aqueous NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-be93220be45842fbbcea0b2b34ecbb70
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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