Triethylamine → (3-Ethyl-4-fluoro-phenylethynyl)-trimethyl-silane

HRID 2415257노트

반응식

HRID 2415257 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[Li+].[Cl-].C(N(CC)CC)C>CN(C)C=O.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.O>[CH2:9]([C:4]1[CH:3]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:10]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 226410254-Bromo-2-ethyl-1-fluorobenzene

생성물 1

HCID 22641049(3-Ethyl-4-fluoro-phenylethynyl)-trimethyl-silane

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 4-bromo-2-ethyl-1-fluoro-benzene (2.4 g, 11.82 mmol) in N,N-dimethylformamide (100 mL), trimethylsilyl acetylene (2.0 mL, 14.19 mmol), PdCl2(PPh3)2 (500 mg, 0.72 mmol), LiCl (1 g, 23.64 mmol), CuI (25 mg, 0.1 mmol) and triethylamine (3 mL) were added and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel (hexanes) to give a brown oil. 1.58 g, 61%.

후처리

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (hexanes)
  5. customto give a brown oil

출처 및 근거

ORD 기록
ord-3abf9204343a4dd98c599d4fb9400c59
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818663B2

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