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

HRID 1597537Notes

Reaction equation

HRID 1597537 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-47c535fcd1b74cb9a8b372e5f13f1b9c
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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