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

HRID 2415257ノート

反応式

HRID 2415257 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-3abf9204343a4dd98c599d4fb9400c59
出典データセット
uspto-grants-2004_11
特許番号
US06818663B2

反応ノート

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