Methanol → Methyl 5-chlorothiophene-2-carboxylate

HRID 1961063Notes

Reaction equation

HRID 1961063 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:15]O>>[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:15])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 589473Methyl 5-chlorothiophene-2-carboxylateYield 99%

Conditions

Temperature
55 °C

Procedure

To a solution of 5-chloro-2-thiophenecarboxylic acid (20 g, 123 mmoles) in MeOH (200 mL) was added conc. H2SO4 (5 mL). After heating to 55° C. for 12 h, the reaction solution was concentrated and diluted with DCM (250 mL). The DCM solution was washed with aqueous NaHCO3, then H2O and dried over Na2SO4. Concentration under vacuum gave the title compound as a yellow oil (21.5 g, 99%): LCMS (ES) m/z 178 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated
  2. additiondiluted with DCM (250 mL)
  3. washThe DCM solution was washed with aqueous NaHCO3
  4. dry with materialH2O and dried over Na2SO4
  5. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-21e4e8b847824c68b0d3a9e48404827d
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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