Dimethylformamide → 5-Cyano-2-fluorobenzaldehyde

HRID 325066ノート

反応式

HRID 325066 の反応式
C(NC(C)C)(C)C.[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.CN(C)[CH:19]=[O:20]>C1COCC1>[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[CH:19]=[O:20]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 145174-Fluorobenzonitrile

生成物 1

HCID 109097255-Cyano-2-fluorobenzaldehyde収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirred, cooled solution (0° C.) of diisopropylamine (15.4 mL, 0.11 mol) in anhydrous tetrahydrofuran (200 mL) n-butyllithium (40 mL of 2.5M in hexane, 0.11 mol) was added from a dropping funnel over a period of 30 min. under argon. The mixture was stirred at that temperature for 30 min. and then cooled to −78° C. A solution of 4-fluoro-benzonitrile (12.1g, 0.1 mol) in dry THF (50 mL) was then added dropwise over 15 min. via syringe and stirred for 1 hour at −78° C. Dimethylformamide (8 mL) was added dropwise from a syringe and the stirring was continued for another 20 min. The reaction was quenched by the rapid addition of acetic acid (20 mL) followed by water (500 mL) and the product was extracted with diethyl ether (2×500 mL). The combined organic layers were washed with 1N HCl, water, saturated sodium chloride and then dried over anhydrous magnesium sulfate, and evaporated to give 2-fluoro-5-cyano-benzaldehyde (11.8 g, 79% yield) as a light yellow solid.

後処理

  1. additionwas added from a dropping funnel over a period of 30 min. under argon
  2. stirringstirred for 1 hour at −78° C
  3. waitthe stirring was continued for another 20 min
  4. customThe reaction was quenched by the rapid addition of acetic acid (20 mL)
  5. extractionthe product was extracted with diethyl ether (2×500 mL)
  6. washThe combined organic layers were washed with 1N HCl, water, saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated

出典と根拠

ORDレコード
ord-2067949aa9864a8ea159138cdaaa5fd8
出典データセット
uspto-grants-2001_04
特許番号
US06221914B1

反応ノート

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