Dimethylformamide → 1-(Difluoromethoxy)-4-(phenylethynyl)benzene

HRID 30545

반응식

HRID 30545 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[CH:2].[F:9][CH:10]([F:19])[O:11][C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1.CN(C)C=O.C(N(CC)CC)C>[Cu]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.O>[F:9][CH:10]([F:19])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:14][CH:13]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 27370081-(Difluoromethoxy)-4-iodobenzene

생성물 1

HCID 574358451-(Difluoromethoxy)-4-(phenylethynyl)benzene수율 76.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

Into a mixture of ethynylbenzene (1.9 g, 18.5 mmol), 1-(difluoromethoxy)-4-iodobenzene (5 g, 18.5 mmol), N,N-dimethylformamide (35 mL), and triethylamine (12.8 mL, 92.6 mmol) was introduced anhydrous argon for 5 minutes. Then, copper(I) iodide (1.85 mmol, 351 mg) and dichlorobis(triphenylphosphine)palladium(II) (1.11, 0.71 g) were added into the mixture and the new mixture was stirred at 60° C. for 3 hours. The mixture cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using hexanes/EtOAc (100/1) as the eluting solvent, gave 1-(difluoromethoxy)-4-(phenylethynyl)benzene as a clear oil (3.45 g, 76% yield). MS m/e M+ 244; 1H NMR (400 MHz, DMSO-d6) 7.2 (d, J=8.78 Hz, 2H), 7.28-7.45 (m, 4H), 7.5-7.55 (m, 2H), 7.6 (d, J=7.78 Hz, 2H).

후처리

  1. additionwas introduced anhydrous argon for 5 minutes
  2. temperatureThe mixture cooled to room temperature
  3. extractionextracted with ethyl ether
  4. dry with materialThe organic extracts were dried over MgSO4
  5. customEvaporation and purification on silica gel (ISCO)

출처 및 근거

ORD 기록
ord-b41d6759d10b4b0cbed807edb4d0b8d3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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