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

HRID 2387717노트

반응식

HRID 2387717 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5ec3ced2816344ee85e869c7732e2cb5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268855B2

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