Triethylamine → 4-(3-Bromo-phenylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

HRID 723046

반응식

HRID 723046 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8](Br)[CH:9]=1)=[O:4].CCN(CC)CC.[Br:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([S:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([Br:21])[CH:23]=2)[CH:9]=1)=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 80597m-BromobenzenethiolHCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylate

생성물 1

HCID 695867774-(3-Bromo-phenylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester수율 99.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-Bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 1 g, 3.75 mmol) and Et3N (523 μL, 3.75 mmol) were dissolved with THF (10 mL) into a round bottom flask with stir bar. To this 3-bromothiophenol (467 μL, 4.51 mmol) was added with stirring. The reaction became turbid therefore additional THF (12 mL) was added. The reaction was stirred at rt for 12 hours. The reaction mixture was concentrated in vacuo and then dissolved into EtOAc. The organic layer was washed several times with saturated NaHCO3 and brine. The combined organic layers were dried over sodium sulfate. Removal of the solvents in vacuo yielded the title compound (1.40 g, quantitative yield), which was used without further purification. 1H-NMR (CDCl3): δ 7.79 (t, 1H, J=1.8 Hz), 7.67–7.70 (m, 1H), 7.54–7.85 (m, 1H), 7.37–7.41 (t, 1H, J=7.9 Hz), 6.87 (s, 1H), 3.88 (s, 1H).

후처리

  1. stirringwith stirring
  2. stirringThe reaction was stirred at rt for 12 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved into EtOAc
  5. washThe organic layer was washed several times with saturated NaHCO3 and brine
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customRemoval of the solvents in vacuo

출처 및 근거

ORD 기록
ord-ce457070815a43bab53edb9d8128ddfa
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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