Ethanol → Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylate

HRID 238070

반응식

HRID 238070 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1B(O)O)=[O:4].Br[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(O[Pd]OC(=O)C)(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:20]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27569932-Bromo-4-fluoro-1-nitrobenzeneHCID 27734962-(Methoxycarbonyl)benzeneboronic acid

생성물 1

HCID 67296936Methyl 5'-fluoro-2'-nitrobiphenyl-2-carboxylate수율 56.9%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 6344Dichloromethane용매

실험 절차

To a microwave vessel was added 2-(methoxycarbonyl)phenylboronic acid (63.4 mg, 0.352 mmol), 2-bromo-4-fluoro-1-nitrobenzene (77 mg, 0.35 mmol), diacetoxypalladium (0.93 mg, 4.1 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.47 mg, 8.45 μmol). Ethanol (1760 μl) and sodium carbonate (176 μl, 0.352 mmol) were added and the mixture was reacted in a microwave reactor at 100° C. for 30 min. The reaction mixture was diluted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate) to provide methyl 5′-fluoro-2′-nitrobiphenyl-2-carboxylate (37a, 54.8 mg, 0.199 mmol, 56.6% yield).

후처리

  1. customthe mixture was reacted in a microwave reactor at 100° C. for 30 min
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography (eluant: 9:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-22c50defc4af4bc28e5d4aa5c8b43360
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642538B2

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