Formic Acid → 2-Bromo-5-methylaniline

4-Bromo-3-nitrotoluene (60.35 g, 279 mmol), 5% by weight platinum carbon (1.09 g, 0.28 mmol) and triethylamine (112.93 g, 1116 mmol) were stirred under heating at 100° C., to which formic acid (99%) (42.39 g, 921 mmol) was added dropwise over 20 minutes. After stirring for 12 hours, it was brought back to room temperature, and then 100 ml of ethyl acetate and 100 ml of water were added thereto. After stirring well, it was filtered through celite to remove platinum carbon. By further adding 200 ml of ethyl acetate and 100 ml of water, it was extracted, the organic phase was washed with water (300 ml×3 times), and dried on magnesium sulfate. The solvent was evaporated to obtain 2-bromo-5-methylaniline (51.30 g, 276 mmol). The yield was 99%.

1. additionwas added dropwise over 20 minutes
2. customwas brought back to room temperature
3. stirringAfter stirring well
4. filtrationit was filtered through celite
5. customto remove platinum carbon
6. additionBy further adding 200 ml of ethyl acetate and 100 ml of water, it
7. extractionwas extracted
8. washthe organic phase was washed with water (300 ml×3 times)
9. customdried on magnesium sulfate
10. customThe solvent was evaporated

ORD record

ord-ca4f5132b0364446a6a6ae3d47bddbb0

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06774245B2