Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

HRID 876534Notes

Reaction equation

HRID 876534 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.[C:12](OC(=O)C)(=[O:14])[CH3:13].OS(O)(=O)=O>O>[C:12]([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:14])[CH3:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69725-Bromosalicylic acidHCID 7918Acetic Anhydride

Product 1

HCID 739225-Bromo-2-acetylsalicylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well-stirred mixture of 5-bromosalicylic acid 29 (200 g, 0.92 mol) and acetic anhydride (210 mL) was added concentrated H2SO4 (0.5 mL). After a few minutes the reaction mixture solidified and was suspended in H2O (1 L). The solid was collected by filtration and washed with H2O. The white solid was dissolved in ethyl acetate (3 L), washed with brine, dried (Na2SO4) and concentrated to give 30 (210 g, 88% yield).

Workup

  1. waitAfter a few minutes the reaction mixture solidified
  2. filtrationThe solid was collected by filtration
  3. washwashed with H2O
  4. dissolutionThe white solid was dissolved in ethyl acetate (3 L)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae659db186b34a6aaae3a5dea89b4149
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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