4-Bromobiphenyl → 5-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol

HRID 84345

반응식

HRID 84345 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:14]([OH:19])[CH2:15][CH2:16][C:17]#[CH:18]>C(N(CC)CC)C.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.[Cu]I>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([C:18]#[C:17][CH2:16][CH2:15][CH2:14][OH:19])=[CH:3][CH:4]=1

참가 물질

6

반응물 2

HCID 71014-BromobiphenylHCID 793464-Pentyn-1-ol

생성물 1

HCID 230493185-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol수율 75%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

반응 조건

온도
65 °C

실험 절차

4-Bromobiphenyl (10.28 g, 44.10 mmol), 4-pentyn-1-ol (4.45 g, 52.92 mmol), and bis(triphenylphosphine)palladium(II) dichloride (310 mg, 0.44 mmol) were stirred in triethylamine (100 mL) under nitrogen for 5 min. Copper(I) iodide (42 mg, 0.22 mmol) was added, and the mixture was stirred for 4 hrs at 65° C. The mixture was cooled to room temperature and filtered through a celite pad, rinsed with ethylacetate. The combined filtrate was evaporated to dryness under reduced pressure. The resulting residue was purified by column chromatography (hexanes:ethylacetate 3:2) to afford 7.78 g of the title compound. Yield: 75%. 1H NMR (300 MHz, CDCl3) δ 1.88 (m, 2H), 2.57 (t, J=6.9 Hz, 2H), 3.84 (t, J=6.0 Hz, 2H), 7.32-7.60 (m, 9H) ppm; 13C NMR (75 MHz, CDCl3) δ 16.4, 31.7, 62.1, 81.2, 90.2, 122.8, 127.0, 127.1, 127.6, 128.9, 132.0, 140.1 ppm.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washrinsed with ethylacetate
  4. customThe combined filtrate was evaporated to dryness under reduced pressure
  5. customThe resulting residue was purified by column chromatography (hexanes:ethylacetate 3:2)

출처 및 근거

ORD 기록
ord-bbfd30650a9148d39f28af8f5a2880c9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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