Tetrahydrofuran → 3-Bromo-2-methyl-5-[3-(trifluoromethyl)phenyl]thiophene

HRID 1257440

반응식

HRID 1257440 반응식
[Br:1][C:2]1[CH:6]=[C:5](Br)[S:4][C:3]=1[CH3:8].[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>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.O>[Br:1][C:2]1[CH:6]=[C:5]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:21])([F:20])[F:9])[CH:16]=2)[S:4][C:3]=1[CH3:8]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 1223733,5-Dibromo-2-methylthiopheneHCID 27343883-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 669394313-Bromo-2-methyl-5-[3-(trifluoromethyl)phenyl]thiophene수율 85.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

Under a nitrogen atmosphere, a mixture of 3,5-dibromo-2-methylthiophene (2.00 g), 3-(trifluoromethyl)phenylboronic acid (2.23 g), tetrakis(triphenylphosphine)palladium (0.45 g), cesium carbonate (5.09 g) and tetrahydrofuran (40 mL) was heated under reflux for 16 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (2.15 g) as a solid.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-99d89984852d4b4d9147b9157afb8d38
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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