Benzene → Ethyl 2-(4-bromophenoxy)benzoate

HRID 444235Notes

Reaction equation

HRID 444235 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.O.[CH:19]1C=CC=C[CH:20]=1>C(O)C.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH2:19][CH3:20])=[O:10])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 19803169HCID 19803169, compound

Product 1

HCID 23464800Ethyl 2-(4-bromophenoxy)benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 560.0 g of 2-(4-bromo-phenoxy)benzoic acid in 1,940 ml of absolute benzene, 218 ml of absolute ethanol and 32.6 ml of concentrated sulfuric acid is refluxed for 32 hours, the water formed being removed in a water separator. The reaction mixture is cooled to 10° and washed, with the addition of ice, with 1,000 ml of water, 500 ml of a 2 N aqueous sodium carbonate solution and then again with 1,000 ml of water. The organic phase is separated off, dried over magnesium sulfate and evaporated at 40° under a pressure of 11 mm Hg. The residue is distilled under a high vacuum and yields ethyl 2-(4-bromo-phenoxy)-benzoate, boiling point 140°-150°/0.05 mm Hg.

Workup

  1. temperatureis refluxed for 32 hours
  2. custombeing removed in a water separator
  3. temperatureThe reaction mixture is cooled to 10°
  4. washwashed, with the addition of ice, with 1,000 ml of water, 500 ml of a 2 N aqueous sodium carbonate solution
  5. customThe organic phase is separated off
  6. dry with materialdried over magnesium sulfate
  7. customevaporated at 40° under a pressure of 11 mm Hg
  8. distillationThe residue is distilled under a high vacuum

Sources & evidence

ORD record
ord-9b8ac4588c854dcaa958b810860e9912
Source dataset
uspto-grants-1981_04
Patent number
US04263315

Reaction notes

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