Hydrochloric Acid → Methyl 4-Bromo-2-chlorobenzoate

HRID 2244320Notes

Reaction equation

HRID 2244320 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.Cl.[CH3:13]O>>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[Cl:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Procedure

3.0 g of 4-bromo-2-chloro-benzoic acid (12.74 mmol) were dissolved in 60 ml methanol and treated with 0.6 ml of concentrated HCl. After 17 h at reflux the reaction mixture was concentrated in vacuo, diluted with DCM and washed with a saturated aqueous NaHCO3 solution and brine, dried with magnesium sulfate, filtered and concentrated in vacuo leading to 2.7 g (85%) of 4-bromo-2-chloro-benzoic acid methyl ester as a light yellow oil. MS (+cEI): 250.0 (M).

Workup

  1. temperatureAfter 17 h at reflux the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with DCM
  4. washwashed with a saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-213d498e38424a1f9b01bff7baf9a1f5
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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