4-Bromo-2,3,5,6-tetrafluoroaniline → 2,3,5,6-Tetrafluoro-4'-octylbiphenyl-4-amine

HRID 601457

반응식

HRID 601457 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)O1.Br[C:25]1[C:30]([F:31])=[C:29]([F:32])[C:28]([NH2:33])=[C:27]([F:34])[C:26]=1[F:35]>>[F:31][C:30]1[C:29]([F:32])=[C:28]([NH2:33])[C:27]([F:34])=[C:26]([F:35])[C:25]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:14]=1

참가 물질

3

반응물 2

HCID 6186714-Bromo-2,3,5,6-tetrafluoroanilineHCID 588233864,4,5,5-Tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane

생성물 1

HCID 866218892,3,5,6-Tetrafluoro-4'-octylbiphenyl-4-amine수율 91.1%

실험 절차

A mixture of 4,4,5,5-tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane (415.0 mg, 1.31 mmol), 4-bromo-2,3,5,6-tetrafluorobenzenamine (213.0 mg, 0.87 mmol), and a quaternary ammonium salt (Aliquat 336, 0.090 g) was degassed three times with nitrogen before dry toluene (7.0 mL) was added. This step was followed by addition of tetrakis(triphenylphosphine) palladium (100.0 mg) and sodium carbonate (aq. 1 M, 4.0 mL), which had been deaerated for 2 hour, under nitrogen. The mixture was stirred vigorously, and heated at reflux for 20 hours. The organic phase of the resulting reaction mixture was filtered through a thin layer of Celite® and evaporated to dryness to give 0.6 g of a crude product. The crude material was purified by chromatography on silica gel (by using ethyl acetate:hexanes (1:9) as the eluent) to yield 2,3,5,6-tetrafluoro-4′-octylbiphenyl-4-amine as an off-white solid (0.280 g, 91% yield).

후처리

  1. customa quaternary ammonium salt (Aliquat 336, 0.090 g) was degassed three times with nitrogen before dry toluene (7.0 mL)
  2. additionwas added
  3. additionThis step was followed by addition of tetrakis(triphenylphosphine) palladium (100.0 mg) and sodium carbonate (aq. 1 M, 4.0 mL), which
  4. temperatureheated
  5. temperatureat reflux for 20 hours
  6. customThe organic phase of the resulting reaction mixture
  7. filtrationwas filtered through a thin layer of Celite®
  8. customevaporated to dryness
  9. customto give 0.6 g of a crude product
  10. customThe crude material was purified by chromatography on silica gel (

출처 및 근거

ORD 기록
ord-c669efc25822460f83a51f4699a8e947
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902363B2

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