Реакция #91032

Уравнение реакции

water

methyl 4-hydroxy-3-methoxy-5-nitrobenzoate

Methyl 4-hydroxy-3-methoxy-5-nitrobenzoate

oxalyl chloride

→

methyl 4-chloro-3-methoxy-5-nitrobenzoate

Выход 68.6%

Methyl 4-chloro-3-methoxy-5-nitrobenzoate

Выход 68.6%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураto cool to RT
2. 2
   workup.STIRRINGstirred for 15 min
3. 3
   ФильтрацияThe precipitate was collected by filtration
4. 4
   Промывкаwashed with water and MeOH

Методика

A solution of methyl 4-hydroxy-3-methoxy-5-nitrobenzoate (2) (4.4 g, 19 mmol) in DMF (30 mL) at 0° C. was treated with oxalyl chloride (5.09 mL, 58.1 mmol) dropwise. The mixture was then stirred at 80° C. for 3 h under a CaCl2 drying tube. The mixture was allowed to cool to RT, poured in to iced water (100 mL) and stirred for 15 min. The precipitate was collected by filtration and washed with water and MeOH to afford methyl 4-chloro-3-methoxy-5-nitrobenzoate (3) (3.2 g, 65% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ: 8.04 (1H, d), 7.77 (1H, d), 4.04 (3H, s), 3.97 (3H, s).

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