Pyridine → 1-(3-Bromo-1-propyn-1-yl)-3-fluorobenzene

HRID 889002ノート

反応式

HRID 889002 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[Br:18]P(Br)Br>C(OCC)C>[Br:18][CH2:10][C:9]#[C:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 27826973-(3-fluorophenyl)prop-2-yn-1-ol

生成物 1

HCID 574296571-(3-Bromo-1-propyn-1-yl)-3-fluorobenzene収率 126%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-2.5 °C

実験手順

3-(3-Fluoro-phenyl)-prop-2-yn-1-ol (0.750 g, 0.005 mol) was taken in diethyl ether (10 ml) containing catalytic amount of pyridine (0.05 ml). The reaction mixture was then cooled to −5-0° C. Tribromo phosphine (0.26 ml, 0.003 mol) was added slowly at −5-0° C. and stirred at the same temperature for 3 hrs. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over Na2SO4, and evaporated under vacuum to get 1-(3-bromo-prop-1-ynyl)-3-fluoro benzene (0.805 gm, 76%).

後処理

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

出典と根拠

ORDレコード
ord-7cb7531f5cea427e912f4b95c07764cd
出典データセット
uspto-grants-2012_08
特許番号
US08252797B2

反応ノート

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