Triethylsilane → Ethyl 5-bromo-2-ethylthiophene-3-carboxylate

HRID 1876987

Reaction equation

HRID 1876987 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7](O)[CH3:8])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[S:6][C:5]([CH2:7][CH3:8])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 68509503HCID 68509503, compound

Product 1

HCID 68515411Ethyl 5-bromo-2-ethylthiophene-3-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of ethyl 5-bromo-2-(1-hydroxyethyl)thiophene-3-carboxylate (11.0 g) synthesized above in trifluoroacetic acid (100 mL) was added dropwise triethylsilane (18.8 mL). After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title compound (9.67 g, 94%) as a pale-yellow oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio)

Sources & evidence

ORD record
ord-481dde5857e24b4090753329b6f77817
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Linked notes

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