Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

HRID 369417Notes

Reaction equation

HRID 369417 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:17]([O:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 69725-Bromosalicylic acidHCID 7918Acetic Anhydride

Product 1

HCID 739225-Bromo-2-acetylsalicylic acid

Procedure

5-Bromosalicylic acid (100 g, 0.46 mol) and acetic anhydride (105 ml) were combined, to which 0.5 ml of concentrated sulfuric acid was added. The resulting mixture solidified in several minutes. Subsequent to suspension in 1,000 ml of water, the solid matter was collected by filtration and then washed with water. The thus-obtained white powder was dried in air and then dissolved in 1,000 ml of ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Subsequent to concentration under reduced pressure, 105 g of 2-acetoxy-5-bromobenzoic acid were obtained as white crystals (yield: 89%).

Workup

  1. additionwas added
  2. waitThe resulting mixture solidified in several minutes
  3. filtrationSubsequent to suspension in 1,000 ml of water, the solid matter was collected by filtration
  4. washwashed with water
  5. customThe thus-obtained white powder was dried in air
  6. dissolutiondissolved in 1,000 ml of ethyl acetate
  7. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationSubsequent to concentration under reduced pressure

Sources & evidence

ORD record
ord-85e0d807cba24fedbe3a0ccf3c8bfa41
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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