Ammonium Chloride → Methyl 2-bromo-4-carbamoylbenzoate

A mixture of 3-bromo-4-(methoxycarbonyl)benzoic acid (2.5 g, 9.69 mmol), NH4Cl (1.04 g, 19.38 mmol), HATU (5.5 g, 14.5 mmol), and DIPEA (5.2 mL, 29.1 mmol) in DCM (50 mL) was stirred for 3 h at rt. Water was added and the mixture was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (3:1) to give methyl 2-bromo-4-carbamoylbenzoate (1.3 g; yield 52%) as a white solid. MS: m/z=257.9 (M+1, ESI+).

1. extractionthe mixture was extracted with DCM
2. washThe combined organic layers were washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography over silica gel
7. washeluted with PE-EA (3:1)

ORD-Eintrag

ord-4d132f5ef33c441382eb69ab88d7f62a

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08546357B2