Water → HCID 23157240, compound

HRID 507972Notes

Reaction equation

HRID 507972 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[CH:8]=1)[CH3:2].[Br:15]Br.O>C(O)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([CH3:14])[C:10]([Br:15])=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 23157571HCID 23157571, compound

Product 1

HCID 23157240HCID 23157240, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-[(3,5-dimethylphenyl)thio]ethyl ethyl ether (2.69 g, 12.8 mmol) in acetic acid (60 mL) was slowly added dropwise a solution of bromine (0.68 mL, 13.2 mmol) in acetic acid (30 mL) under stirring at room temperature. The reaction mixture was stirred at the same temperature for 2 hr, poured into cold water, and the mixture was extracted with diethyl ether. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1) to give the title compound (2.41 g, yield 65%) as a pale-yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 2 hr
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-0acafe846a3a4ed3b5284a35aa7e3847
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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