Réaction #1772050

Équation de réaction

Water

Acetyl chloride

3-bromophenol

pyridine

→

3-bromophenyl acetate

Rendement 96.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionthe organic layer was extracted with dichloromethane
2. 2
   LavageThe combined organic layers were washed with 2.5N NaHSO4, 3N NaOH, water, brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   ConcentrationConcentration

Mode opératoire

Acetyl chloride (10.2 mL, 144 mmol) was added in a dropwise manner over 1 h to a cold (ice bath) solution of 3-bromophenol (25 g, 144 mmol) and pyridine (10.8 mL, 144 mmol) in dichloromethane (100 mL), and the reaction was stirred 18 hr at room temperature. Water (150 mL) was added and the organic layer was extracted with dichloromethane. The combined organic layers were washed with 2.5N NaHSO4, 3N NaOH, water, brine, and dried over Na2SO4, and filtered. Concentration gave the 3-bromophenyl acetate as a pink liquid (28 g, 96%). GC-MS data: 214 (M+); 1H NMR (DMSO-d6): 7.37-7.39 (d, 1H), 7.26-7.30 (m, 2H), 7.04-7.07 (t, 1H), 2.30 (s, 3H).

Source