반응 #2501403

반응 방정식

ammonium chloride

4-bromoisophthalic acid dimethyl ester

Copper(I) cyanide

→

4-cyanoisophthalic acid dimethyl ester

수율 80.0%

용매

DMF

반응 조건

후처리

1. 1
   온도The slurry solution was heated
2. 2
   온도at reflux temperature for one hour
3. 3
   기타White precipitate was formed
4. 4
   추출Then it was extracted with ethyl acetate
5. 5
   건조The combined extracts were dried over sodium sulfate
6. 6
   기타Removal of solvent
7. 7
   기타gave white solid which
8. 8
   세척was washed with cold methanol

실험 절차

To a solution of 4-bromoisophthalic acid dimethyl ester 202 (2.95 g, 10.8 mmol) in anhydrous DMF (50 ml), Copper(I) cyanide (1.20 g, 13.5 mmol) was added in one portion. The slurry solution was heated at reflux temperature for one hour. When the solution was cooled to ambient temperature, it was poured into 300 mL of ammonium chloride solution (10%) at 0° C. White precipitate was formed. The slurry solution was stirred at ambient temperature for 30 minutes. Then it was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate. Removal of solvent gave white solid which was washed with cold methanol to give 1.89 g (80%) of 4-cyanoisophthalic acid dimethyl ester 203: 1H NMR (400 MHz, CDCl3) δ 3.95 (s, 3H), 4.05 (s, 3H), 7.91 (d, J=8 Hz, 1H), 8.30 (dd, J=1.7 Hz, J=8 Hz, 1H), 8.77 (d, J=1.7 Hz, 1H).

출처