Ammonium Chloride → ({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

HRID 2184352노트

반응식

HRID 2184352 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:9][CH:8]=1

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

생성물 1

HCID 22476627({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

A well stirred suspension of 4.0 g (12.2 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 0.23 g (1.22 mmol) of cuprous iodide and 0.856 mg (1.22 mmol) of dichloro bis(triphenylphosphine) palladium(II) in a mixture of 20 ml THF and 10 ml triethylamine is treated dropwise with 1.44 g (14.6 mmol) of trimethylsilyl acetylene. The reaction is exothermic. The mixture is stirred overnight at RT, treated with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The organic phase is dried, concentrated and subjected to flash-chromatography (silica gel, cyclohexane) to yield 3.48 g (95%) of a slightly orange oil. NMR (CDCl3; 300 MHz): 0.24 ppm (s, 9H); 5.06 ppm (s, 2H); 6.85-7.45 ppm (m, 8H).

후처리

  1. stirringThe mixture is stirred overnight at RT
  2. extractionextracted three times with ethyl acetate
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customto yield 3.48 g (95%) of a slightly orange oil

출처 및 근거

ORD 기록
ord-4e7f55ff111443c98ea684cd3c74b685
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900354B2

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