Potassium Iodide → Tert-butyl-[2-(4-chloro-3-fluoro-phenoxy)-ethoxy]-dimethyl-silane

HRID 1728072노트

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HRID 1728072 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)C>[C:25]([Si:22]([O:21][CH2:20][CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:9])[CH:4]=1)([CH3:24])[CH3:23])([CH3:28])([CH3:27])[CH3:26]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27245234-Chloro-3-fluorophenolHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

생성물 1

HCID 57566201Tert-butyl-[2-(4-chloro-3-fluoro-phenoxy)-ethoxy]-dimethyl-silane수율 69%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 4-chloro-3-fluoro-phenol (10 g, 68 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (19 g, 136 mmol), potassium iodide (11 g, 68 mmol), and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (18 g, 75 mmol, Aldrich). The reaction mixture was heated at 100° C. for 24 h. The crude was cooled, diluted with ethyl ether, washed with water, NaHCO3 solution, and brine. The organic layer was separated, dried over Na2SO4, and concentrated. The filtrate was concentrated and the residue was purified by chromatography (EtOAc:Hexanes=1:20) to give tert-butyl-[2-(4-chloro-3-fluoro-phenoxy)-ethoxy]-dimethyl-silane as colorless oil (Yield 14 g, 69%).

후처리

  1. temperatureThe crude was cooled
  2. washwashed with water, NaHCO3 solution, and brine
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by chromatography (EtOAc:Hexanes=1:20)

출처 및 근거

ORD 기록
ord-6d1f28e424544d0b93dac8c5e1f71b92
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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