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

HRID 1914536Notes

Reaction equation

HRID 1914536 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:9][CH:10]=1)=[O:5])[CH3:2].[Cl:17]N1C(=O)CCC1=O>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:9][C:10]=1[Cl:17])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58110324Ethyl 5-phenylthiophene-3-carboxylate

Product 1

HCID 581102772-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl esterYield 76.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl-2-phenylthiophen-4-carboxylate (0.5 g, 2.15 mmol) was dissolved in acetic acid (5 mL). N-chlorosuccinimide (2.17 mmol) was added and the reaction stirred overnight. The reaction was concentrated under vacuum and purified by flash chromatography on silica, eluting with 0%-50% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.44 g). 1H NMR (400 MHz, CHCl3-d): δ 7.5 (d, 2H), 7.4-7.25 (m, 4H), 4.4 (q, 2H), 1.4 (t, 3H).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. custompurified by flash chromatography on silica
  3. washeluting with 0%-50% ethyl acetate in cyclohexane
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-475846909e2545a7998e5017ad100819
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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