Ammonium Chloride → Dimethyl 4-cyano-1,3-benzenedicarboxylate

HRID 33737

반응식

HRID 33737 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11](Br)=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[Cu][C:17]#[N:18].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([C:17]#[N:18])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 2824912Dimethyl 4-bromoisophthalateHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 10376118Dimethyl 4-cyano-1,3-benzenedicarboxylate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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).

후처리

  1. temperatureThe slurry solution was heated
  2. temperatureat reflux temperature for one hour
  3. customWhite precipitate was formed
  4. extractionThen it was extracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. customRemoval of solvent
  7. customgave white solid which
  8. washwas washed with cold methanol

출처 및 근거

ORD 기록
ord-929552fcd0e54714a95f0ed2e4b01384
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429651B2

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