Trimethylsilylacetylene → 3-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

HRID 913897

反応式

HRID 913897 の反応式
[Br:1][C:2]1[C:3](I)=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>C(N(CC)CC)C.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>[Br:1][C:2]1[C:3]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 575461423-Bromo-2-iodo-5-(trifluoromethyl)aniline

生成物 1

HCID 575462013-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

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
80 °C

実験手順

3-Bromo-2-iodo-5-(trifluoromethyl)aniline (18.7 g, 51.1 mmol) was dissolved in triethylamine (400 mL). To this was added dichlorobis(triphenylphosphine)palladium(II) (3.59 g, 5.11 mmol), copper(I) iodide (0.973 g, 5.11 mmol), and trimethylsilylacetylene (5.52 g, 56.2 mmol). The reaction was stirred for 2 h at ambient temperature, at 80° C. for 2 h, and then evaporated. The residue was purified by chromatography on silica gel with 5% ethyl acetate/hexanes to give 10.67 g (62.1%) as a brown liquid. 1H-NMR (CDCl3, 400 MHz) δ 7.13 (s, 1H), 6.82 (s, 1H), 4.52 (bs, 2H), 0.29 (s, 9H); LC/MS (HPLC method 4): tR=4.208 min, 336.05(MH)+.

後処理

  1. customevaporated
  2. customThe residue was purified by chromatography on silica gel with 5% ethyl acetate/hexanes
  3. customto give 10.67 g (62.1%) as a brown liquid

出典と根拠

ORDレコード
ord-007ea7fb7a5d426b94102d884d1b418c
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

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