N-bromobutanimide → Ethyl2-bromo-5-ethylthiophene-3-carboxylate

HRID 1809080Notes

Reaction equation

HRID 1809080 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][CH:7]=1)=[O:5])[CH3:2].[Br:13]N1C(=O)CCC1=O>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[Br:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12588559Ethyl 5-ethylthiophene-3-carboxylate

Product 1

HCID 12588560Ethyl2-bromo-5-ethylthiophene-3-carboxylateYield 40.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Ethyl-thiophene-3-carboxylic acid ethyl ester (1.2 g, 6.52 mmol) was dissolved in acetic acid (10 mL). N-Bromosuccinimide (7.1 mmol) was added and the reaction was stirred for 4 hours. The solvent was removed under vacuum and the product purified by flash chromatography on silica, eluting with 0%-30% t-butylmethylether in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.7 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. customThe solvent was removed under vacuum
  2. customthe product purified by flash chromatography on silica
  3. washeluting with 0%-30% t-butylmethylether in cyclohexane
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-0f2932e620cc4794a9915029368df4d7
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

Loading…