Phenol → Phenyl 5-bromo-2-hydroxybenzoate

HRID 980426Notes

Reaction equation

HRID 980426 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1.[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC=CC=1>[Br:5][C:6]1[CH:14]=[C:10]([C:11]([O:13][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 69725-Bromosalicylic acidHCID 24386Thionyl Chloride

Product 1

HCID 266984Phenyl 5-bromo-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

80 ml of thionyl chloride was gradually added to a benzene suspension of 217 g of 5-bromosalicyclic acid and 113 g of phenol, followed by refluxing for ten hours under heating. After distilling off the benzene, ice-water was added to the residue, and the precipitate formed was collected by filtration, followed by drying. Yield: 210 g.

Workup

  1. temperatureby refluxing for ten hours
  2. temperatureunder heating
  3. distillationAfter distilling off the benzene, ice-water
  4. additionwas added to the residue
  5. customthe precipitate formed
  6. filtrationwas collected by filtration
  7. customby drying

Sources & evidence

ORD record
ord-fff0888236b54b86aff40ea01a9b6ec8
Source dataset
uspto-grants-1987_01
Patent number
US04637902

Reaction notes

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