Trimethylsilylacetylene → 2-Bromo-4-(trifluoromethyl)-6-[2-(trimethylsilyl)ethynyl]benzenamine

HRID 855281ノート

反応式

HRID 855281 の反応式
[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5](I)[C:3]=1[NH2:4].[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>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[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:3]=1[NH2:4]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 269862642-Bromo-6-iodo-4-(trifluoromethyl)aniline

生成物 1

HCID 693432912-Bromo-4-(trifluoromethyl)-6-[2-(trimethylsilyl)ethynyl]benzenamine収率 94%

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2 回

実験手順

To a solution of 7.54 g of 2-bromo-6-iodo-4-(trifluoromethyl)-aniline (21 mmol) in 70 ml triethylamine were added 723 mg of Pd(PPh3)2Cl2 (1 mmol), 196 mg of CuI (1 mmol) and 3.14 ml of ethinyltrimethylsilane (23 mmol). The reaction mixture was stirred for 3 h at rt before the triethylamine was removed under reduced pressure. Then DCM was added and the resulting suspension was filtered. The filtrate was then concentrated and the residue purified by chromatography (silica gel; c-hexane/EtOAc 19:1) to yield 6.51 g (94%) of 2-bromo-4-trifluoromethyl-6-trimethylsilanylethynyl-phenylamine as a dark brown liquid. 1H NMR (CDCl3, 300 MHz): δ 0.28 (s, 9H), 4.99 (br s, 2H), 7.51 (s, 1H), 7.61 (s, 1H).

後処理

  1. customwas removed under reduced pressure
  2. additionThen DCM was added
  3. filtrationthe resulting suspension was filtered
  4. concentrationThe filtrate was then concentrated
  5. customthe residue purified by chromatography (silica gel; c-hexane/EtOAc 19:1)

出典と根拠

ORDレコード
ord-d08cc1fb0b3b41309198afba0b3baa6c
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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