Hydrochloric Acid → Ethyl 4-[5-(4-trifluoromethylphenyl)-2-thienyl]benzoate

HRID 1354426노트

반응식

HRID 1354426 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.I[C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1.Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]([C:22]3[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=3)=[CH:12][CH:13]=2)=[CH:7][CH:8]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 142891Ethyl 4-iodobenzoateHCID 121680562-[4-(Trifluoromethyl)phenyl]thiopheneHCID 178418339Butyllithium

생성물 1

HCID 22934543Ethyl 4-[5-(4-trifluoromethylphenyl)-2-thienyl]benzoate수율 45%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution (7 ml) of 2-(4-trifluoromethylphenyl) thiophene (1.71 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 5.00 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (14 ml) of zinc chloride (1.09 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and ethyl 4-iodobenzoate (1.16 ml) and tetrakis(triphenylphosphine)palladium (0.202 g) were added. This mixture was stirred overnight under an argon atmosphere and poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. Ethanol (200 ml) was added to the residue, and the mixture was heated under reflux for 10 min. Insoluble materials were filtered off, and the filtrate was concentrated to give ethyl 4-[5-(4-trifluoromethylphenyl)-2-thienyl]benzoate (1.19 g, yield 45%) as a yellow crystalline powder. melting point: 203–204° C.

후처리

  1. stirringThis mixture was stirred overnight under an argon atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. additionEthanol (200 ml) was added to the residue
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 10 min
  9. filtrationInsoluble materials were filtered off
  10. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-dad12fbbd49c4f5bb795bd62e7296fcf
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223791B2

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