Реакция #57529

Уравнение реакции

Triethylamine

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

2,4-dichloro-benzoyl chloride

→

desired product

Выход 84.0%

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

Выход 84.0%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

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

Методика

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).

Источник