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

HRID 2086677Notes

Reaction equation

HRID 2086677 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-abd942f31bcb4c02ad69ac90abd59fbc
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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