反应 #91020

反应方程式

tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

tert-Butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate

boron trichloride

water

NaHCO3

→

4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid

收率 24.0%

溶剂

DCM

DCM

反应条件

后处理

1. 1
   workup.WAITat RT for 2 h
2. 2
   温度The reaction mixture was cooled to 0° C.
3. 3
   过滤The resulting white precipitate was collected by filtration
4. 4
   洗涤washed with water (2 mL)
5. 5
   其他The solid was dried
6. 6
   其他purified by capture and release on SAX
7. 7
   洗涤eluting with 5% AcOH in THF

实验过程

A solution of tert-butyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methoxybenzoate (5) (55 mg, 0.13 mmol) in DCM (5 mL) was cooled to 0° C. and treated dropwise with a solution of 1 M boron trichloride in DCM (349 μL, 349 μmol). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction mixture was cooled to 0° C. and water (0.5 mL) and sat. aq. NaHCO3 (2 mL) were added. The resulting white precipitate was collected by filtration and washed with water (2 mL). The solid was dried, then purified by capture and release on SAX, eluting with 5% AcOH in THF to afford 4-(3,5-dichloro-4-ethoxybenzamido)-2-hydroxybenzoic acid (AAA-057) (11 mg, 24%) as a white solid: m/z 370 [M+H]+ (ES+), 368 [M−H]− (ES−); 1H-NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, s), 8.06 (2H, s), 7.76 (1H, d), 7.48 (1H, d), 7.28 (1H, dd), 4.14 (2H, q), 1.91 (1H, s), 1.40 (3H, t), 1.35 (1H, s).

来源