Triphenylphosphine → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 1257436

반응식

HRID 1257436 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Zn]Cl.[Cl-].[NH4+]>Cl[Pd]Cl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:12]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477798HCID 178477798, 화합물

생성물 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylate수율 1,830.4%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of the compound (1.80 g) obtained in Example 128a, palladium chloride(II) (0.02 g), triphenylphosphine (0.07 g) and tetrahydrofuran (30 mL) was added MeZnCl (2M tetrahydrofuran solution, 9.5 ml), and the mixture was heated under reflux for 4 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride 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 (1.07 g) as a colorless solid.

후처리

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

출처 및 근거

ORD 기록
ord-5f3bca02527d470a924e211a0b5035a5
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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