Tetrahydrofuran → 2-(1-Undecynyl)fluorobenzene

HRID 235181

반응식

HRID 235181 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O1CCCC1.C(N(CC)CC)C>C(OCC)(=O)C.[Cu]I>[C:9]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8])#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 612591-Bromo-2-fluorobenzene2회HCID 752491-Undecyne

생성물 1

HCID 183730212-(1-Undecynyl)fluorobenzene수율 53.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

To a solution of 2-bromofluorobenzene (17.5 g), 1-undecyne (18.3 g), tetrahydrofuran (50 ml), and triethylamine (70 ml) was added bistriphenylphosphine palladium(II)chloride (1.2 g) and copper(I) iodide (162 mg). The reaction mixture was stirred at 55° C. for 3 hr, and an additional 2-bromofluorobenzene (2.0 g) and bistriphenylphosphine palladium(II)chloride (200 mg) were added. The mixture was stirred at 55° C. overnight, allowed to cool to room temperature, diluted with ethyl acetate and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed over silica gel (eluted with hexane). The appropriate fractions were collected and evaporated. The residue was distilled twice under vacuum to give 13.1 g (53%) of product.

후처리

  1. stirringThe mixture was stirred at 55° C. overnight
  2. temperatureto cool to room temperature
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed over silica gel (eluted with hexane)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. distillationThe residue was distilled twice under vacuum

출처 및 근거

ORD 기록
ord-c57da39cfede4c2aa93d3082f6ede134
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597838

연결된 노트

불러오는 중…