Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

HRID 2190902Notes

Reaction equation

HRID 2190902 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].OS(O)(=O)=O>>[C:12]([O:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 69725-Bromosalicylic acidHCID 7918Acetic Anhydride

Product 1

HCID 739225-Bromo-2-acetylsalicylic acidYield 93.3%

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-hydroxy-5-bromo-benzoic acid (5.0 g, 23.0 mmol) in acetic anhydride (7.1 mL, 75.4 mmol) was added conc. H2SO4 (0.35 mL) at rt. Resulting suspension was heated in a 100° C. oil bath for 25 min. After cooled to about 50° C., the reaction mixture was poured onto ice (100 g) with stirring. The precipitated product was collected, rinsed with water, and dried in vacuo to give the title compound (5.56 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.21 (d, J=2.3 Hz, 1H), 7.71 (dd, J=8.6, 2.3 Hz, 1H), 7.01 (d, J=8.6 Hz, 1H), 2.34 (s, 3H).

Workup

  1. customResulting suspension
  2. temperatureAfter cooled to about 50° C.
  3. additionthe reaction mixture was poured onto ice (100 g)
  4. customThe precipitated product was collected
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6d61ebf1c05041de9233e8607232fc96
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

Loading…