Methanol → HCID 57826680, compound

HRID 1961121Notes

Reaction equation

HRID 1961121 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([OH:12])=[O:11])[S:5][C:6]=1[CH2:7][CH2:8][CH3:9].S(=O)(=O)(O)O.O.[CH3:19]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:19])=[O:11])[S:5][C:6]=1[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 38431344-bromo-5-propylthiophene-2-carboxylic acid

Product 1

HCID 57826680HCID 57826680, compoundYield 93%

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-5-propyl-2-thiophenecarboxylic acid (5.0 g, 20.07 mmol) in methanol (100 ml) was added sulfuric acid (5.35 ml, 100 mmol). The resulting solution stirred at 50° C. for 36 h. H2O (50 mL) was added the aqueous phase was washed several times with DCM. The combined organic fractions were washed with saturated NaHCO3, dried over Na2SO4, concentrated and used directly without further purification providing methyl 4-bromo-5-propyl-2-thiophenecarboxylate (5.1 g, 18.61 mmol, 93% yield) as a yellow oil: LCMS (ES) m/e 262, 264 (M, M+2)+.

Workup

  1. washwas washed several times with DCM
  2. washThe combined organic fractions were washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customused directly without further purification

Sources & evidence

ORD record
ord-dcf99f27d9be4edaa57def977f9fd034
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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