1,4-Dibromobenzene → 1,4-Bis[(trimethylsilyl)ethynyl]benzene

HRID 590630

반응식

HRID 590630 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C1COCC1>[CH3:9][Si:10]([C:13]#[C:14][C:2]1[CH:7]=[CH:6][C:5]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

참가 물질

6

반응물 2

HCID 78041,4-DibromobenzeneHCID 66111Trimethylsilylacetylene

생성물 1

HCID 5224921,4-Bis[(trimethylsilyl)ethynyl]benzene수율 92%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

40 mL THF was transferred to a flame-dried Schlenk flask. 1,4-dibromobenzene (2.5 mmol, 0.060 g), Pd(PPh3)4 (0.1 mmol 0.12 g), and CuI (0.2 mmol, 0.004 g) were added. Trimethylsilylacetylene (6 mmol, 0.87 mL) and 10 mL DIPA was added via syringe. The mixture was heated to 45° C. for 24 hrs. under nitrogen. The resulting suspension was filtered and filtrate was concentrated under reduced pressure. The residual solid was dissolved in dichloromethane and washed with an aqueous ammonium chloride solution. The organic layer was concentrated and crude product was subjected to column chromatography (silica, hexanes) to afford a white solid (2.3 mmol, 0.61 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ: 7.37 (s, 4H), 0.22 (s, 18H).

후처리

  1. filtrationThe resulting suspension was filtered
  2. concentrationfiltrate was concentrated under reduced pressure
  3. dissolutionThe residual solid was dissolved in dichloromethane
  4. washwashed with an aqueous ammonium chloride solution
  5. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-1f8f9d829e824e3b966d7709d0fd338e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09234003B2

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