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

HRID 1914540노트

반응식

HRID 1914540 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-90eec9a2808348f4a8dd4a7d5f6a494f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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