1-Nitropropane → Tert-butyl 2-fluoro-5-(1-nitropropyl)benzoate

HRID 1364315노트

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HRID 1364315 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N+:46]([CH2:49][CH2:50][CH3:51])([O-:48])=[O:47]>C(COC)OC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:15][C:5]1[CH:4]=[CH:3][C:2]([CH:49]([N+:46]([O-:48])=[O:47])[CH2:50][CH3:51])=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

참가 물질

7

반응물 4

HCID 79031-NitropropaneHCID 62657Potassium Phosphate, TribasicHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 63896644Tert-butyl 5-bromo-2-fluorobenzoate

생성물 1

HCID 86246594Tert-butyl 2-fluoro-5-(1-nitropropyl)benzoate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To tert-butyl 5-bromo-2-fluorobenzoate (1.26 g) in dimethoxyethane (22.9 ml) solution, tris(dibenzylideneacetone)dipalladium (0.10 g), 2-(di-tert-butylphosphino)-2′-methylbiphenyl (0.14 g), tripotassium phosphate (1.07 g), and 1-nitropropane (0.82 ml) were added, the mixture was stirred at room temperature for 1 minute, then the mixture was stirred under heating and reflux for 15 hours. The insoluble compound was filtered out, then the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate, ethyl acetate: 0 to 10%) to obtain the title compound (392 mg).

후처리

  1. stirringthe mixture was stirred
  2. temperatureunder heating
  3. temperaturereflux for 15 hours
  4. filtrationThe insoluble compound was filtered out
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate, ethyl acetate: 0 to 10%)

출처 및 근거

ORD 기록
ord-30896ba3634b4123a24a18d793b4b26a
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888348B2

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