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

HRID 2387707ノート

反応式

HRID 2387707 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

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 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.

後処理

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

出典と根拠

ORDレコード
ord-950a422e5b914f02bfe9e2318c5ee95f
出典データセット
uspto-grants-2012_09
特許番号
US08268855B2

反応ノート

読み込み中…