Sulfuric Acid → HCID 608316, compound

HRID 2377462Notes

Reaction equation

HRID 2377462 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH:16](O)([CH3:18])[CH3:17]>O>[CH:16]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 114563-Bromobenzoic acid

Product 1

HCID 608316HCID 608316, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-bromo benzoic acid (Aldrich, 2.4 g, 11.9 mmol) in isopropanol (20 mL) was treated with 1 mL of concentrated sulfuric acid and the resulting reaction mixture was refluxed overnight. The reaction mixture was then cooled to ambient temperature and diluted with water and extracted with diethyl ether. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound as an oil (2.54 g, 88%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil that

Sources & evidence

ORD record
ord-39662e260ba34a9e98fa045aaca6fb5f
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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