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

HRID 30545

反応式

HRID 30545 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 574358451-(Difluoromethoxy)-4-(phenylethynyl)benzene収率 76.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b41d6759d10b4b0cbed807edb4d0b8d3
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

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