Calcium Carbonate → 4-Bromo-2-fluoro-5-methylaniline

To a slurry of 2-fluoro-5-metylaniline (6.75 g, 54 mmol) and CaCO3 (10 g, 100 mmol) in CH2Cl2 (1 L) and MeOH (400 mL) was added a solution of Benzyltrimethylammonium tribromide (22.3 g, 57 mmol) in CH2Cl2 (180 mL) and MeOH (70 mL). The solution was added dropwise and the mixture was stirred over night. The solution was a light orange/tan color. The mixture was filtered and the solvent was removed under reduced pressure. The resulting slurry was diluted with H2O (100 mL) and extracted with Et2O (3×200 mL). The mixture was purified by flash column chromatography (Hex:Et2O 2:1 to Et2O) to provide (9 g, 69.5% yield) the product as a white solid. 1H-NMR (DMSO-d6) δ 7.23 (d, J=10.8 Hz, 1H), 6.74 (d, J=10.8 Hz, 1H), 5.27 (s, 2H), 2.20 (s, 3H).

1. additionThe solution was added dropwise
2. filtrationThe mixture was filtered
3. customthe solvent was removed under reduced pressure
4. additionThe resulting slurry was diluted with H2O (100 mL)
5. extractionextracted with Et2O (3×200 mL)
6. customThe mixture was purified by flash column chromatography (Hex:Et2O 2:1 to Et2O)

ORD record

ord-5241948d3a464064aefa81c422b79e4a

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143393B2