Reacción #1869213

Ecuación de reacción

methanol

2-(2,4-dimethoxyphenyl)-N-methylacetamide

BBr3

→

2-(4-hydroxy-2-methoxyphenyl)-N-methylacetamide

subtitled compound

2-(2-Hydroxy-4-methoxyphenyl)-N-methylacetamide

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter addition
2. 2
   Otrowere removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   Lavadowashed successively with aqueous NaHCO3 and H2O
5. 5
   SecadoThe organic layer was dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane)

Procedimiento

To a solution of 2-(2,4-dimethoxyphenyl)-N-methylacetamide (445 mg, 2.12 mmol) in CH2Cl2 (10 mL) was slowly added 1M BBr3 solution in CH2Cl2 (6.4 mL, 6.4 mmol). After addition was completed, the reaction mixture was stirred at 0° C. for 2.5 h, methanol (2 mL) was added and after 15 min the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-5% methanol in dichloromethane) to give the subtitled compound (16 mg) along with 2-(4-hydroxy-2-methoxyphenyl)-N-methylacetamide (30 mg).

Fuente