Reaction #1145563

Reaction equation

water

N-hydroxysuccinimide

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

3-bromo-4-(methoxycarbonyl)benzoic acid

→

2-bromo-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzoic acid methyl ester

Yield 99.6%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Concentrationthe solution was concentrated in vacuo
2. 2
   Otherto remove tetrahydrofuran
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   Dryingthe extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated under reduced pressure

Procedure

A solution of 3-bromo-4-(methoxycarbonyl)benzoic acid (Example 76; 1.60 g, 6.2 mmol) in tetrahydrofuran (30 mL) was cooled to 10° C. and N-hydroxysuccinimide (781 mg, 6.8 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g, 6.5 mmol) were added. The solution was allowed to stir at room temperature overnight, then water was added and the solution was concentrated in vacuo to remove tetrahydrofuran. The mixture was extracted with ethyl acetate and the extracts were dried (MgSO4), filtered and evaporated under reduced pressure to furnish 2-bromo-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzoic acid methyl ester (2.20 g, quantitative yield).

Source