반응 #1994296

반응 방정식

4-chloro-2-fluorobenzaldehyde

sodium hydroxide

acetone

dichloromethane

→

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

수율 76.0%

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

수율 76.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The aqueous layer was separated
3. 3
   추출extracted with CH2Cl2 (100 mL)
4. 4
   세척the combined organic extracts were washed with brine
5. 5
   건조dried over magnesium sulfate (MgSO4)
6. 6
   기타Solvent removal
7. 7
   workup.DISTILLATIONfollowed by Kugelrohr distillation

실험 절차

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.

출처