3-Bromo-4-chlorobenzoic acid → Ethyl 3-bromo-4-chlorobenzoate

HRID 2410078Notes

Reaction equation

HRID 2410078 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].Cl.O1CCO[CH2:15][CH2:14]1>C(O)C>[CH2:14]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Br:1])[CH:3]=1)[CH3:15]

Participants

4

Reactant 2

HCID 27355443-Bromo-4-chlorobenzoic acidHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 12594300Ethyl 3-bromo-4-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-bromo-4-chlorobenzoic acid (5.0 g, 21 mmol) in 150 mL absolute ethanol was added 15 mL of 4N HCl/dioxane. The mixture was heated to reflux for 24 hours then cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and H2O, and the separated organic phase was washed sequentially with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (DMSO-d6) δ 8.22 (d, 1H), 7.94 (dd, 1H), 7.80 (d, 1H), 4.33 (q, 2H), 1.33 (t, 3H); MS (DCI+) m/z 263 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and H2O
  5. washthe separated organic phase was washed sequentially with saturated NaHCO3 solution, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b084406b31734f4eb02a9e1141febe02
Source dataset
uspto-grants-2014_08
Patent number
US08815930B2

Reaction notes

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