Ethanol → Ethyl 3-bromo-4-fluorobenzoate

HRID 401789Notes

Reaction equation

HRID 401789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16][CH2:17]O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 705093-Bromo-4-fluorobenzoic acid

Product 1

HCID 24770261Ethyl 3-bromo-4-fluorobenzoateYield 90.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 3-bromo-4-fluoro-benzoic acid (430 g, 1.97 mol, 1 eq) in EtOH (2.3 L) was added dropwise thionyl chloride (287 mL, 3.94 mol, 2 eq) at 10° C. Then the mixture was heated to reflux overnight. The mixture was concentrated in vacuum to give a residue. The residue was dissolved in ethyl acetate (800 mL), washed with aqueous sodium hydrogen carbonate, brine (300 mL) and water (200 mL), then concentrated in vacuo to give title compound as a white solid (440 g, 1.78 mol, 90.3%).

Workup

  1. temperatureThen the mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated in vacuum
  4. customto give a residue
  5. washwashed with aqueous sodium hydrogen carbonate, brine (300 mL) and water (200 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37187ffc81f7461590429120a506fa00
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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