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

HRID 1930306ノート

反応式

HRID 1930306 の反応式
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

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 68984776HCID 68984776、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a432874ef411409fa020589fb6343476
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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