Methyl 5-bromothiophene-2-carboxylate → Methyl 5-(3-tert-butyl-4-methoxyphenyl)-2-thiophenecarboxylate

HRID 1857872노트

반응식

HRID 1857872 반응식
[C:1]([C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Mg].Br[C:16]1[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=1>C1COCC1.[Cl-].[Zn+2].[Cl-]>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 37338984-Bromo-2-tert-butyl-1-methoxybenzeneHCID 5462224Magnesium

생성물 1

HCID 15382605Methyl 5-(3-tert-butyl-4-methoxyphenyl)-2-thiophenecarboxylate

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2 g (8.2 mmol) of 3-tert-butyl-4-methoxybromobenzene is added dropwise to a suspension of 300 mg (12 mmol) of magnesium in 10 ml of THF. Once the addition is complete, the mixture is refluxed for one hour. At room temperature, 1.35 g (9.9 mmol) of anhydrous zinc chloride are added and the mixture is stirred for one hour. 1.2 g (5.5 mmol) of methyl 5-bromo-2-thiophenecarboxylate and 60 mg (0.12 mmol) of the NiCl2 /DPPE complex are then added successively and the mixture is left stirring at room temperature for 12 hours. The reaction medium is poured into ice-water and extracted with ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is chromatographed on a column of silica eluted with a mixture of hexane and dichloromethane (50/50% by volume). After evaporation of the solvents, 1.56 g (93%) of the expected methyl ester are collected, with a melting point of 94-5° C.

후처리

  1. additionOnce the addition
  2. temperaturethe mixture is refluxed for one hour
  3. waitthe mixture is left
  4. stirringstirring at room temperature for 12 hours
  5. extractionextracted with ethyl ether
  6. customthe organic phase is separated out after settling
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customThe residue obtained
  10. customis chromatographed on a column of silica
  11. washeluted with a mixture of hexane and dichloromethane (50/50% by volume)
  12. customAfter evaporation of the solvents, 1.56 g (93%) of the expected methyl ester
  13. customare collected, with a melting point of 94-5° C.

출처 및 근거

ORD 기록
ord-88ee3ec8da9f4be59b78983432c4c2cb
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147255

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