Sulfuric Acid → 2-(Acetyloxy)-4-bromobenzoic acid

HRID 2190913Notes

Reaction equation

HRID 2190913 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].S(=O)(=O)(O)O>>[C:12]([O:11][C:4]1[CH:3]=[C:2]([Br:1])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 2687374-Bromo-2-hydroxybenzoic acid

Product 1

HCID 5403732-(Acetyloxy)-4-bromobenzoic acid

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-hydroxy-benzoic acid (12.35 g, 56.91 mmol), acetic anhydride (35.6 mL) and conc sulfuric acid (0.93 mL) was heated at 100° C. for 1 h; then cooled, poured into 400 g ice/water, stirred for several minutes, the white precipitates were collected with filtration, washed with water, then the white solids were oven vacuum dried at 50° C. for 3 days to give the desired product (11.62 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.95 (d, 1H, J=8.5 Hz), 7.48 (dd, 1H, J=2.0 Hz, 8.5 Hz), 7.32 (d, 1H, J=2.0 Hz).

Workup

  1. temperaturethen cooled
  2. customthe white precipitates
  3. filtrationwere collected with filtration
  4. washwashed with water
  5. customdried at 50° C. for 3 days

Sources & evidence

ORD record
ord-05dc2ed44521447387b2c7ac9fdbba09
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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