Sulfuric Acid → Phenol, 3-bromo-, 1-acetate

HRID 1993768Notes

Reaction equation

HRID 1993768 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Br:6])[CH:8]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 115633-Bromophenol

Product 1

HCID 141946Phenol, 3-bromo-, 1-acetate

Procedure

Concentrated sulfuric acid (0.3 mL) was added to a stirred mixture of 3-bromophenol (26.2 g) and acetic anhydride (15 mL). An exothermic reaction took place, after which the mixture was allowed to cool to RT. Acetic acid and excess acetic anhydride were evaporated, and the residue was poured onto ice. The mixture was extracted with ether, and the combined ether extracts were washed with brine, then dried over magnesium sulfate and concentrated to afford 3-bromophenyl acetate (compound 6a, 31.6 g) as an amber oil.

Workup

  1. customAn exothermic reaction
  2. customAcetic acid and excess acetic anhydride were evaporated
  3. additionthe residue was poured onto ice
  4. extractionThe mixture was extracted with ether
  5. washthe combined ether extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02dc2a9d6a7241ea9b0f64fc4d4a4e10
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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