Methanol → Methyl 4-bromothiophene-2-carboxylate

HRID 1845403Notes

Reaction equation

HRID 1845403 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-a9b1d8d8ed924a0db216d3b4a112aa0e
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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