Reaktion #57529

Reaktionsgleichung

Triethylamine

1-(4-Bromo-2-hydroxy-phenyl)-ethanone

2,4-dichloro-benzoyl chloride

→

desired product

Ausbeute 84.0%

2,4-dichloro-benzoic acid 2-acetyl-5-bromo-phenyl ester

Ausbeute 84.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise over 30 minutes
2. 2
   EinengenAfter this time, the reaction mixture was concentrated via rotary evaporation
3. 3
   workup.DISSOLUTIONdissolved in EtOAc
4. 4
   Waschenwashed twice with water and once with a saturated NaHCO3 solution
5. 5
   TrocknenThe organic portion was dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

Triethylamine (14.6 mL, 104.6 mmol) was added to a solution of 1-(4-Bromo-2-hydroxy-phenyl)-ethanone (15.0 g, 96.8 mmol) dissolved in dichloromethane (200 mL). The resulting solution was cooled to 0° C. at which time 2,4-dichloro-benzoyl chloride, dissolved in 50 mL dichloromethane was added dropwise over 30 minutes. The resulting mixture was allowed to warm to ambient temperature and stir at this temperature for an additional 16 hours. After this time, the reaction mixture was concentrated via rotary evaporation and then dissolved in EtOAc and washed twice with water and once with a saturated NaHCO3 solution. The organic portion was dried (MgSO4), filtered and concentrated to give the desired product (22.7 g, 84%) which was used without further purification. 1H-NMR (DMSO) δ 8.18 (d, 1H), 7.96 (d, 1H), 7.82 (s, 1H), 7.64 (m, 3H), 2.53 (s, 3H).

Quelle