Benzene → HCID 57424272, compound

HRID 1870042Notes

Reaction equation

HRID 1870042 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.O.[CH:18]1[CH:23]=CC=C[CH:19]=1>C(O)(C)C>[CH:18]([O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([Br:1])[CH:10]=[C:9]([Br:11])[CH:8]=1)([CH3:23])[CH3:19]

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 1118Sulfuric AcidHCID 12063Benzoic acid, 3,5-dibromo-

Product 1

HCID 57424272HCID 57424272, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3,5-dibromobenzoic acid (Aldrich, 2.4 g, 8.6 mmol) in benzene (150 mL) and isopropanol (50 mL) was treated with concentrated sulfuric acid (2 mL) and heated to reflux overnight using a Dean-Stark water trap. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The organic phase was washed with water and saturated, aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a clear oil that was used as such for the next step (2.7 g, ˜100%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with diethyl ether
  6. washThe organic phase was washed with water
  7. dry with materialsaturated, aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-fb75f8dcbc2d453884c4d655fe2eb27e
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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