Methanol → Methyl 5-chlorothiophene-2-carboxylate

HRID 2391970Notes

Reaction equation

HRID 2391970 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-carboxylate

Conditions

Temperature
50 °C

Procedure

To a solution of 5-chloro-2-thiophenecarboxylic acid (2.0 g, 12.3 mmol) in dry MeOH (75 mL) was added H2SO4 (1 mL). The reaction mixture was heated to 50° C. for 20 h and was then concentrated under vacuum. The residue was dissolved in DCM and washed several times with saturated NaHCO3 solution. The organic fraction was dried (Na2SO4), concentrated under vacuum and used directly without further purification 21.3 g, quant.): LC-MS (ES) m/z=177 (M+H)+.

Workup

  1. concentrationwas then concentrated under vacuum
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed several times with saturated NaHCO3 solution
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customused directly without further purification 21.3 g

Sources & evidence

ORD record
ord-f1ed784ea1544746b71006b40e86d1cb
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

Loading…