Methanol → Methyl 4-bromothiophene-2-carboxylate

HRID 1961031Notes

Reaction equation

HRID 1961031 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[S:5][CH:6]=1.OS(O)(=O)=O.[OH-].[Na+].[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:17])=[O:8])[S:5][CH:6]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 6104094-Bromo-2-thiophenecarboxylic Acid

Product 1

HCID 12752071Methyl 4-bromothiophene-2-carboxylate

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-2-thiophenecarboxylic acid (4 g, 19 mmol) in MeOH (100 mL) was added H2SO4 (5 mL) dropwise at 25° C. The solution was stirred for 12 h at 50° C. and was poured into ice-H2O and the pH was adjusted to ˜11 with aqueous NaOH. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly (4.27 g, quant.): LCMS (ES) m/z 222 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted several times with DCM
  2. dry with materialthe combined organic fractions were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e313844c6a31437a82e131d24ec8e1f8
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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