Toluene → 2-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester

HRID 2068602ノート

反応式

HRID 2068602 の反応式
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][CH:18]=1)=[O:13])[CH3:10].C1(C)C=CC=CC=1>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][C:18]=1[Br:1])=[O:13])[CH3:10]

参加物

5

反応物 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 58110324Ethyl 5-phenylthiophene-3-carboxylate

生成物 1

HCID 581102722-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester収率 56.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

N-Bromosuccinimide (1.22 g, 6.83 mmol) was added to a solution of ethyl-2-phenylthiophen-4-carboxylate (6.83 mmol) in acetic acid (10 mL) and stirred overnight. Toluene was added and the solvent was removed under vacuum. The product was purified by flash chromatography on silica, eluting with 0%-10% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (1.2 g). LCMS m/z 312.52 [M+H]+ R.T.=4.55 mins (Analytical Method 5).

後処理

  1. customthe solvent was removed under vacuum
  2. customThe product was purified by flash chromatography on silica
  3. washeluting with 0%-10% ethyl acetate 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-b57593dda4e8431c94186f1b3f09c094
出典データセット
uspto-grants-2012_10
特許番号
US08299063B2

反応ノート

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