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

HRID 2387717ノート

反応式

HRID 2387717 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].C(N(CC)CC)C.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C1COCC1.[Cu](I)I.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>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:9]=1)[C:5]#[N:6]

参加物

7

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 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of commercially available 3-bromo-5-fluorobenzonitrile (5 g, 25 mmol) and triethylamine (35 ml) in 35 ml of THF was bubbled nitrogen for 10 min. Then added trimethylsilylacetylene (5.0 g, 50 mmol), copper iodide (60 mg, 0.31 mmol), and PdCl2(PPh3)2 (80 mg, 0.11 mmol) and the reaction mixture was heated with a heating mantle. After an initial exotherm, the reaction was heated at reflux for 3 hrs. The reaction mixture was concentrated on a rotary evaporator and the dark residue diluted with hexane and washed with water three times. The hexane layer was filtered through Celite and the filtrate was concentrated to give a brown oil. The crude material was used without further purification. LCMS B: Ret time 3.96 min, (M+H)+=218.14. 1H NMR, 400 MHz, CDCl3: 7.57 (s, 1H), 7.43 (m, 1H), 7.35 (m, 1H), 0.26 (s, 9H).

後処理

  1. temperatureAfter an initial exotherm, the reaction was heated
  2. temperatureat reflux for 3 hrs
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. additionthe dark residue diluted with hexane
  5. washwashed with water three times
  6. filtrationThe hexane layer was filtered through Celite
  7. concentrationthe filtrate was concentrated
  8. customto give a brown oil
  9. customThe crude material was used without further purification
  10. customRet time 3.96 min, (M+H)+=218.14

出典と根拠

ORDレコード
ord-5ec3ced2816344ee85e869c7732e2cb5
出典データセット
uspto-grants-2012_09
特許番号
US08268855B2

反応ノート

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