反応 #1994296

反応方程式

4-chloro-2-fluorobenzaldehyde

sodium hydroxide

acetone

dichloromethane

→

4-(4-chloro-2-fluorophenyl)-3-buten-2-one

収率 76.0%

(E)-4-(4-chloro-2-fluorophenyl)-but-3-en-2-one

収率 76.0%

溶媒

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The aqueous layer was separated
3. 3
   抽出extracted with CH2Cl2 (100 mL)
4. 4
   洗浄the combined organic extracts were washed with brine
5. 5
   乾燥dried over magnesium sulfate (MgSO4)
6. 6
   その他Solvent removal
7. 7
   workup.DISTILLATIONfollowed by Kugelrohr distillation

実験手順

To a mechanically stirred solution of 4-chloro-2-fluorobenzaldehyde (23.8 grams (g), 0.15 mole (mol)) in acetone (100 milliliters (mL)) at room temperature was added over 20 minutes (min) a solution of sodium hydroxide (NaOH, 6.6 g, 0.165 mol) in water (H2O, 400 mL). After stirring the reaction mixture overnight, dichloromethane (CH2Cl2, 100 mL) was added. The aqueous layer was separated and extracted with CH2Cl2 (100 mL), and the combined organic extracts were washed with brine and dried over magnesium sulfate (MgSO4). Solvent removal followed by Kugelrohr distillation gave 4-(4-chloro-2-fluorophenyl)-3-buten-2-one (1; 22.5 g, 76%) as a colorless liquid, which solidified upon standing: by 70-80° C., 0.1 mmHg (13.33 pascals (Pa)); 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=16.5 Hz, 1H), 7.50 (t, J=8.1 Hz, 1H), 7.22-7.12 (m, 2H), 6.76 (d, J=16.5 Hz, 1H), 2.39 (s, 3H); HRMS-ESI (m/z): calcd for C10H8ClFO, 198.024. found 198.025.

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