Trimethylsilylacetylene → Ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate

HRID 1930306노트

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HRID 1930306 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:7]=1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 68984776HCID 68984776, 화합물

생성물 1

HCID 69088386Ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate수율 62.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

Ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (1.00 g, 3.27 mmol), PdCl2(PPh3)2 (115 mg, 0.16 mmol), CuI (44 mg, 0.23 mmol), and trimethylsilylacetylene (0.7 mL, 4.9 mmol) were dissolved in Et3N (5 mL). The mixture was immediately degassed by vacuum, and the flask was charged with N2. The mixture was heated overnight at 50° C. Water was added and then the solution was extracted with EtOAc (3×). The organic was washed with NH4Cl, brine and dried (MgSO4). The solvent was removed and then the residue was purified by silica gel column chromatography to obtain ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate (0.66 g, 62% yield).

후처리

  1. customThe mixture was immediately degassed by vacuum
  2. additionthe flask was charged with N2
  3. additionWater was added
  4. extractionthe solution was extracted with EtOAc (3×)
  5. washThe organic was washed with NH4Cl, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a432874ef411409fa020589fb6343476
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188113B2

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