Reacción #1869210

Ecuación de reacción

2-Methoxybenzylamine

acetic anhydride

→

subtitled compound

Rendimiento 40.4%

N-(2-Hydroxybenzyl)acetamide

Rendimiento 40.4%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe volatiles were removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   workup.ADDITION1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly
4. 4
   workup.ADDITIONAfter addition
5. 5
   Temperaturacooled to 0° C.
6. 6
   workup.ADDITIONmethanol (3 mL) was added and after 10 min volatiles
7. 7
   Otrowere removed in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
9. 9
   Lavadowashed successively with aqueous NaHCO3 and H2O
10. 10
    SecadoThe organic layer was dried over Na2SO4
11. 11
    Filtraciónfiltered
12. 12
    Concentraciónconcentrated
13. 13
    OtroThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum spirit)

Procedimiento

2-Methoxybenzylamine (822 mg, 6.0 mmol) in methanol (10 mL) was treated with acetic anhydride (613 mg, 6.0 mmol) at room temperature for 2 h. The volatiles were removed in vacuo. The residue was dissolved in CH2Cl2, cooled to 0° C., 1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly. After addition was completed the reaction mixture was stirred at room temperature overnight, cooled to 0° C., methanol (3 mL) was added and after 10 min 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 (0-50% ethyl acetate in petroleum spirit) to give the subtitled compound (400 mg).

Fuente