Methylamine → 2-(2-bromo-5-fluorophenyl)-N-methylacetamide

Temperature

0 °C

Thionyl chloride (9.4 mL, 129 mmol) is added to a solution of (2-bromo-5-fluoro-phenyl)-acetic acid (20.0 g, 85.8 mmol) in dry toluene (400 mL). The mixture is heated at reflux for 4 hours and the solvent is removed in vacuo. The remanence is redissolved in dry toluene (400 mL) and cooled to 0° C. 40% methylamine (aq.) (17.7 mL, 515 mmol) is added dropwise at 0-5° C. The mixture is then stirred at ambient temperature for 16 hours, poured onto water (250 mL) and extracted with ethyl acetate (3×200 mL). The combined organic fractions are washed successively with saturated sodium bicarbonate solution (150 mL) and brine (150 mL), dried (MgSO4) and concentrated in vacuo. This gives 16.2 g (77%) of crystalline 2-(2-bromo-5-fluoro-phenyl)-N-methyl-acetamide.

1. temperatureThe mixture is heated
2. temperatureat reflux for 4 hours
3. customthe solvent is removed in vacuo
4. dissolutionThe remanence is redissolved in dry toluene (400 mL)
5. additionpoured onto water (250 mL)
6. extractionextracted with ethyl acetate (3×200 mL)
7. washThe combined organic fractions are washed successively with saturated sodium bicarbonate solution (150 mL) and brine (150 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-b6e812f499ba45c1aca82db1ea90cfb4

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629473B2