Potassium Carbonate → HCID 59298838, compound

HRID 2234862Notes

Reaction equation

HRID 2234862 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 80597m-Bromobenzenethiol

Product 1

HCID 59298838HCID 59298838, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (52.9 mmol) of 3-bromothiophenol are placed in the presence of 9.4 ml (63.5 mmol) of ethyl bromoisobutyrate and 8 g (57.9 mmol) of K2CO3 in 100 ml of EtOH. This mixture is stirred at reflux for 4 h and then dry concentrated. The residue is taken up in water. After extraction in AcOEt and then drying on MgSO4, the organic phases are dry concentrated. The oil obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 90:10) and 11a is isolated in the form of clear oil (16.8 g, quantitative yield). TLC silica gel 60 F 254 Merck, petroleum ether:AcOEt 90:10, Rf=0.72.

Workup

  1. temperatureat reflux for 4 h
  2. customdry
  3. concentrationconcentrated
  4. extractionAfter extraction in AcOEt
  5. customdrying on MgSO4
  6. customthe organic phases are dry
  7. concentrationconcentrated
  8. customThe oil obtained
  9. customis purified by flash chromatography on silica (petroleum ether:AcOEt 90:10)

Sources & evidence

ORD record
ord-82c53e7de65f4b68923e8179e4dd6991
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

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