Methanol → Methyl 2-Bromo-5-chlorobenzoate

HRID 2174676Notes

Reaction equation

HRID 2174676 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.O.[CH3:18]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 890272-Bromo-5-chlorobenzoic acid

Product 1

HCID 280500Methyl 2-Bromo-5-chlorobenzoate

Procedure

2-bromo-5-chlorobenzoic acid (4 g, 0.016 mol) was dissolved in MeOH (20 ml) and sulphuric acid (1 ml) was added. The reaction was refluxed for 3 h then cooled at RT. Water (20 ml) was added and the solid was filtered, dissolved in DCM and washed with saturated aqueous solution of NaHCO3. The organic solvent was dried (Na2SO4) and evaporated to obtain 4.17 g of the title compound as oil.

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. filtrationthe solid was filtered
  3. dissolutiondissolved in DCM
  4. washwashed with saturated aqueous solution of NaHCO3
  5. dry with materialThe organic solvent was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-acd162e96f324485a7ea004735bdf60b
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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