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

HRID 855281노트

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HRID 855281 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d08cc1fb0b3b41309198afba0b3baa6c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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