Ethanol → Ethyl 4-bromothiophene-2-carboxylate

HRID 1892079Notes

Reaction equation

HRID 1892079 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[S:9][CH:10]=1.[CH2:14](O)[CH3:15]>>[Br:5][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:9][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 6104094-Bromo-2-thiophenecarboxylic Acid

Product 1

HCID 10847330Ethyl 4-bromothiophene-2-carboxylate

Conditions

Temperature
65 °C

Procedure

Thionyl chloride (8.8 mL, 121 mmol) was added slowly to a solution of 4-bromothiophene-2-carboxylic acid (5.0 g, 24.2 mmol) in ethanol (30 mL) at room temperature. The reaction mixture was warmed up to 65° C. and stirred for 4 hours. Removal of solvent and excess reagent under vacuum afforded the crude product ethyl 4-bromothiophene-2-carboxylate (1015), which was used in the next step without further purification.

Workup

  1. customRemoval of solvent and excess reagent under vacuum

Sources & evidence

ORD record
ord-7a8388d6647045e3882eb90d6eac45f3
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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