Tetrahydrofuran → 2-(1-Undecynyl)fluorobenzene

HRID 235181

反応式

HRID 235181 の反応式
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]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 612591-Bromo-2-fluorobenzene2 回HCID 752491-Undecyne

生成物 1

HCID 183730212-(1-Undecynyl)fluorobenzene収率 53.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c57da39cfede4c2aa93d3082f6ede134
出典データセット
uspto-grants-1997_01
特許番号
US05597838

関連ノート

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