Phenylacetyl chloride → N-(4-bromophenyl)-2-phenylacetamide

Temperature

25 °C

In a 250-mL round-bottom flask was placed a mixture of 4-bromoaniline (6.90 g, 40.1 mmol), triethylamine (16.8 g, 166 mmol), 4-dimethylaminopyridine (200 mg, 1.64 mmol), and 2-phenylacetyl chloride (6.50 g, 42.1 mmol) in dichloromethane (150 mL). The resulting mixture was stirred for 12 hours at 25° C. The reaction was then quenched by the addition of 50 mL of water. The organic layer was separated, and the aqueous layer was extracted with 2×50 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel column, 100:1 to 10:1 CH2Cl2/MeOH) to provide the title compound as a light yellow solid.

1. customIn a 250-mL round-bottom flask was placed
2. customThe reaction was then quenched by the addition of 50 mL of water
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with 2×50 mL of dichloromethane
5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe residue was purified by flash column chromatography (silica gel column, 100:1 to 10:1 CH2Cl2/MeOH)

ORD record

ord-bcc16b2427464448aade1cfbb11b3b27

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309222B2