反応 #2501403

反応方程式

ammonium chloride

4-bromoisophthalic acid dimethyl ester

Copper(I) cyanide

→

4-cyanoisophthalic acid dimethyl ester

収率 80.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度The slurry solution was heated
2. 2
   温度at reflux temperature for one hour
3. 3
   その他White precipitate was formed
4. 4
   抽出Then it was extracted with ethyl acetate
5. 5
   乾燥The combined extracts were dried over sodium sulfate
6. 6
   その他Removal of solvent
7. 7
   その他gave white solid which
8. 8
   洗浄was washed with cold methanol

実験手順

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).

出典