Chlorosuccinimide → 2-Chloro-5-ethyl-thiophene-3-carboxylic acid ethyl ester

HRID 1809084Notes

Reaction equation

HRID 1809084 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][CH:15]=1)=[O:13])[CH3:10]>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[C:17]([CH2:19][CH3:20])[S:16][C:15]=1[Cl:1])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 12588559Ethyl 5-ethylthiophene-3-carboxylate

Product 1

HCID 595425792-Chloro-5-ethyl-thiophene-3-carboxylic acid ethyl esterYield 69.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Chlorosuccinimide (0.8 g, 5.9 mmol) was added to a solution of 5-ethyl-thiophene-3-carboxylic acid ethyl ester (1 g, 5.43 mmol) in acetic acid (10 mL) and stirred overnight. The reaction was filtered and the solvent removed under vacuum. The product was purified by flash chromatography on silica, eluting with 0%-100% t-butylmethyl ether in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.83 g). 1H NMR (400 MHz, CHCl3-d): δ 7.05 (s, 1H), 4.3 (q, 2H), 2.75 (q, 2H), 1.4 (t, 3H), 1.3 (t, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent removed under vacuum
  3. customThe product was purified by flash chromatography on silica
  4. washeluting with 0%-100% t-butylmethyl ether in cyclohexane
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-0346fc020d8a4f0da45d3906449986b0
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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