Реакция #91020

Уравнение реакции

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

Выход 24.0%

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   workup.WAITat RT for 2 h
2. 2
   ТемператураThe reaction mixture was cooled to 0° C.
3. 3
   ФильтрацияThe resulting white precipitate was collected by filtration
4. 4
   Промывкаwashed with water (2 mL)
5. 5
   ДругоеThe solid was dried
6. 6
   Другоеpurified by capture and release on SAX
7. 7
   Промывкаeluting with 5% AcOH in THF

Методика

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).

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