Triethylamine → 3-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

HRID 17104노트

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HRID 17104 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:9]=1)[C:5]#[N:6]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 27833303-Bromo-5-fluorobenzonitrile

생성물 1

HCID 167372113-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
95 °C

실험 절차

A solution of 3-bromo-5-fluorobenzonitrile (2.5 g, 12.5 mmol), (trimethylsilyl)acetylene (2.86 ml, 20 mmol), bis(acetate)bis(triphenylphoshpino) Palladium(II) (936 mg, 1.25 mmol) and triethylamine (35 ml) in toluene (35 ml) was 15 degassed by bubbling nitrogen through the solution and then stirred at 95° C. for 30 minutes. Filtration and concentration to yield a crude product. It was diluted with EtOAc (150 ml). The organic phase was washed with saturated NaHCO3 solution (50 ml), brine (50 ml) and the organic layer was dried over sodium sulfate. Filtration and concentration to yield a product A293.1 (2.4 g, 88%). HPLC: 95%, retention time: 4.05 minute (condition A). LC/MS (M+H)+=218.2.

후처리

  1. customdegassed
  2. customby bubbling nitrogen through the solution
  3. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-bd280274d3164bc1abeaa913cf194cbf
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

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