Triethylamine → (4-Fluorophenyl){4-[(4-fluorophenyl)ethynyl]phenyl}methanone

HRID 380712

反応式

HRID 380712 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)#[CH:2].Br[C:11]1[CH:25]=[CH:24][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:11]2[CH:12]=[CH:13][C:14]([C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[CH:24][CH:25]=2)=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanoneHCID 5226271-Ethynyl-4-fluorobenzene

生成物 1

HCID 5303262(4-Fluorophenyl){4-[(4-fluorophenyl)ethynyl]phenyl}methanone収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

Into a 250 mL, 3-neck, round-bottom flask equipped with a magnetic stirrer, a thermocouple, and a condenser were placed 12.00 g (100.0 mMol) of 1-ethynyl-4-fluorobenzene, 27.93 g (100.0 mMol) of 4-bromo-4′-fluorobenzophenone (Rieke Metals, Inc.), 1.5 g of tetrakis(triphenylphosphine)palladium[0], and 150 mL of de-aerated triethylamine. The reaction mixture was heated to 80° C. with stirring under argon for 3 hr and then cooled to ambient overnight (16 hr) with stirring. The reaction mixture was filtered to remove a white precipitate of triethylamine hydrobromide. The triethylamine solvent was evaporated and the solids obtained were dissolved in dichloromethane. The resulting solution was washed with water (2×50 mL), 2% HCl (2×50 mL), brine, and then dried over sodium sulfate. After removal of the solvent, the crude 4-fluoro-4′-(4-fluorobenzoyl)tolane was purified by silica gel column chromatography using hexanes as the elutant. White crystals having a melting point of 190-191° C. were obtained in a yield of 81%.

後処理

  1. customInto a 250 mL, 3-neck, round-bottom flask equipped with a magnetic stirrer
  2. temperaturecooled to ambient overnight (16 hr)
  3. stirringwith stirring
  4. filtrationThe reaction mixture was filtered
  5. customto remove a white precipitate of triethylamine hydrobromide
  6. customThe triethylamine solvent was evaporated
  7. customthe solids obtained
  8. washThe resulting solution was washed with water (2×50 mL), 2% HCl (2×50 mL), brine
  9. dry with materialdried over sodium sulfate
  10. customAfter removal of the solvent
  11. customthe crude 4-fluoro-4′-(4-fluorobenzoyl)tolane was purified by silica gel column chromatography
  12. customwere obtained in a yield of 81%

出典と根拠

ORDレコード
ord-534401a7aa6f48f5abc629d65fd846f1
出典データセット
uspto-grants-2001_10
特許番号
US06303733B1

関連ノート

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