N-bromobutanimide → Methyl 5-(bromomethyl)thiophene-2-carboxylate

HRID 650670

반응식

HRID 650670 반응식
COC(C1SC(C)=CC=1)=O.BrN1C(=O)CCC1=O.[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH:28](Br)[Br:29])=[CH:26][CH:27]=1)=[O:22]>C(Cl)(Cl)(Cl)Cl>[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][Br:29])=[CH:26][CH:27]=1)=[O:22]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 580756Methyl 5-methyl-2-thiophenecarboxylateHCID 24179893Methyl 5-(dibromomethyl)thiophene-2-carboxylate

생성물 1

HCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate수율 25%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

5-Methyl-thiophene-2-carboxylic acid methyl ester (20.0 g, 0.13 mol) was dissolved in a suspension of N-bromosuccinimide (45.4 g, 0.26 mol) and 2,2′-aza-bis-isobutyronitrile (0.1 g, 0.61 mmol) in 1 L of carbon tetrachloride. The suspension was refluxed for 48 hours then cooled and the precipitate was filtered off. The filtrate was concentrated and the residue was purified on silica gel (100% hexanes then 9:1 Hexanes-Ethyl acetate) to provide a 26 g fraction containing mainly the di-brominated compound 5-dibromomethyl-thiophene-2-carboxylic acid methyl ester as a yellow oil and a more polar fraction (7.5 g) containing mainly compound T-1 (25% yield) as a yellow oil (70% purity).

후처리

  1. temperatureThe suspension was refluxed for 48 hours
  2. temperaturethen cooled
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified on silica gel (100% hexanes
  6. custom9:1 Hexanes-Ethyl acetate) to provide a 26 g fraction
  7. additiona more polar fraction (7.5 g) containing mainly compound T-1 (25% yield) as a yellow oil (70% purity)

출처 및 근거

ORD 기록
ord-b123d0dea85948b8834e85b7e638c417
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274620B1

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