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

HRID 396789Notes

Reaction equation

HRID 396789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[C:19](OC(=O)C)(=[O:21])[CH3:20]>O>[C:19]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 115633-BromophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 141946Phenol, 3-bromo-, 1-acetateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-bromophenol (25 g, 145 mmol) in acetic anhydride (14 ml) was added a few drop of sulfuric acid, and the mixture was stirred for 2 hours. The mixture was poured into a solution of NaHCO3 (1.3 g, 15.5 mmol) in water (160 ml). The whole was extracted with diethylether. The organic layer was washed with saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo. The residue was used for next reaction without purification. (31 g, 99% yield).

Workup

  1. extractionThe whole was extracted with diethylether
  2. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was used for next reaction without purification

Sources & evidence

ORD record
ord-d03daa0cdf5640529f69289a7f618800
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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