반응 #2352353

반응 방정식

water

Phosgene

Hünig's base

2-Amino-4,5-dichloro-benzoic acid

→

product

수율 94.7%

3,4-Dichloroisatoic anhydride

수율 94.7%

용매

DCM THF

반응 조건

후처리

1. 1
   온도warmed slowly to rt
2. 2
   추출extracted with DCM (3×) and EtOAc (2×)
3. 3
   건조The combined organic layers were dried (MgSO4)
4. 4
   농축concentrated

실험 절차

2-Amino-4,5-dichloro-benzoic acid (1.5 g, 7.28 mmol) was dissolved in 1:1 DCM/THF (20 mL) and cooled to 0° C. Phosgene (20% in toluene, 5.4 mL, 8.00 mmol) and Hünig's base (2.54 mL, 14.6 mmol) were added and the reaction was stirred overnight and warmed slowly to rt. The mixture was poured into water and extracted with DCM (3×) and EtOAc (2×). The combined organic layers were dried (MgSO4), and concentrated to provide the product as a white solid (1.6 g, 92%). HPLC: RT=8.10 min. MS (ESI−): mass calcd. for C8H3Cl2NO3, 232.0; m/z found, 231 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 11.95 (s, 1H), 8.10 (s, 1H), 7.32 (s, 1H).

출처