p-Toluenesulfonic acid monohydrate → Methyl 5-bromo-2-fluorobenzoate

HRID 606820Notes

Reaction equation

HRID 606820 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 21525435Methyl 5-bromo-2-fluorobenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a solution of 5-bromo-2-fluorobenzoic acid (20 g, 92 mmol) and p-toluenesulfonic acid monohydrate (52 g, 275 mmol) in methanol (200 mL) at reflux overnight. Concentrate and dissolve the residue in ethyl acetate, wash twice with an aqueous saturated solution of sodium bicarbonate, once with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter and concentrate to give the title compound as a clear liquid (19.7 g, 92%).

Workup

  1. temperatureat reflux overnight
  2. concentrationConcentrate
  3. dissolutiondissolve the residue in ethyl acetate
  4. washwash twice with an aqueous saturated solution of sodium bicarbonate, once with an aqueous saturated solution of sodium chloride
  5. dry with materialdry (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-07f3bccf4e4b47a295cac74a81b95760
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…