Potassium Carbonate → HCID 62804946, compound

HRID 602794Notes

Reaction equation

HRID 602794 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>C(OCC)C>[CH3:14][O:13][C:11](=[O:12])[CH2:10][S:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 80597m-Bromobenzenethiol

Product 1

HCID 62804946HCID 62804946, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 8.0 g (42 mmol) of 3-bromothiophenol was treated with 7.1 g (47 mmol) of methyl bromoacetate and potassium carbonate. The resulting suspension was stirred at reflux for 24 hrs, cooled to RT and neutralized with a saturated aqueous solution of NH4Cl. Diethylether was added, the phases were separated and the aqueous one was extracted twice with diethylether. The combined organic phases were dried over Na2SO4, filtered and evaporated to give 12.1 g (99%) of (3-bromo-phenylsulfanyl)-acetic acid methyl ester as a light yellow oil, MS: 279 (MNH4+, 1Br).

Workup

  1. temperatureat reflux for 24 hrs
  2. customthe phases were separated
  3. extractionthe aqueous one was extracted twice with diethylether
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-32dcfe7c405c47f483fa96bed84642ae
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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