Ammonium fluoride → 8-(2-Fluorophenyl)-l-benzocyclooctanone

HRID 1491966ノート

反応式

HRID 1491966 の反応式
Br[CH:2]1[CH2:9][CH2:8][C:7]2[C:10](=[O:14])[CH2:11][CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4][CH2:3]1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Sn](CCCC)(CCCC)CCCC.[F-].[NH4+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:2]1[CH2:9][CH2:8][C:7]2[C:10](=[O:14])[CH2:11][CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4][CH2:3]1

参加物

7

反応物 3

HCID 25516Ammonium fluorideHCID 150471822-FluorophenyltributyltinHCID 190368668-Bromo-l-benzocyclooctanone

生成物 1

HCID 676471588-(2-Fluorophenyl)-l-benzocyclooctanone収率 40%

試薬・触媒・溶媒 3

HCID 92152Silver(II) oxide触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

In 10 ml of dimethylformamide were dissolved 2.0 g (7.9 mmol) of 8-bromo-l-benzocyclooctanone, 0.27 g (0.23 mmol) of tetrakis(triphenylphosphine) palladium and 2.0 g (8.6 mmol) of silver oxide, 4.6 g (11.9 mmol) of o-fluorophenyltributyl tin was added thereto, and the mixture was stirred under an argon atmosphere at 120° C for 2 hours. After cooling, an aqueous solution of ammonium fluoride was added to the reaction solution, and then stirred at room temperature for 12 hours. The reaction solution was filtered through celite, washed with ethyl acetate and water, and then extracted. The organic layer was washed with saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then separated and purified by silica gel column chromatography [elution solvent: hexane-ethyl acetate (9:1)]to obtain 0.84 g (40%) of the desired compound.

後処理

  1. additionwas added
  2. temperatureAfter cooling
  3. stirringstirred at room temperature for 12 hours
  4. filtrationThe reaction solution was filtered through celite
  5. washwashed with ethyl acetate and water
  6. extractionextracted
  7. washThe organic layer was washed with saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customseparated
  11. custompurified by silica gel column chromatography [
  12. washelution solvent

出典と根拠

ORDレコード
ord-bc80b5ab606d46ab91f0b69e0c42cbf4
出典データセット
uspto-grants-1994_12
特許番号
US05371225

反応ノート

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