Reaction #1124304

Reaction equation

3-bromo-4-(methoxycarbonyl)benzoic acid

NH4Cl

HATU

DIPEA

→

methyl 2-bromo-4-carbamoylbenzoate

Yield 52.0%

Solvents

Water

DCM

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with DCM
2. 2
   WashThe combined organic layers were washed with brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was purified by column chromatography over silica gel
7. 7
   Washeluted with PE-EA (3:1)

Procedure

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+).

Source