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

HRID 1809080ノート

反応式

HRID 1809080 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 12588560Ethyl2-bromo-5-ethylthiophene-3-carboxylate収率 40.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0f2932e620cc4794a9915029368df4d7
出典データセット
uspto-grants-2013_01
特許番号
US08362008B2

反応ノート

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