Hydrochloric Acid → 2-Nitro-4-trifluoromethylanisole

HRID 1871071

반응식

HRID 1871071 반응식
[CH3:1][O-:2].[Na+].[N+](CC)([O-])=O.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].Cl>CS(C)=O>[CH3:1][O:2][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6587NitroethaneHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 10942334Sodium Methoxide

생성물 1

HCID 967482-Nitro-4-trifluoromethylanisole수율 117.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
16.5 °C

실험 절차

Sodium methoxide (1.35 g; 25 mmol; 2.5 equiv) was slurried in DMSO (10 mL) and cooled in a cool water bath. Nitroethane (0.79 mL; 11 mmol; 1.1 equiv.) and 4-chloro-3-nitrobenzotrifluoride (1; 1.49 mL; 10 mmol) were mixed and added slowly dropwise with cooling such that the temperature remained between 15 and 20° C. After the addition was complete, the reaction mixture was allowed to warm slowly over 3 h from 15 to 18° C. and then stirred overnight at 18° C. to completely consume 1 according to GC analysis. Toluene (10 mL) was added and the mixture was cooled in ice water and 3 N HCl (10 mL; 30 mmol; 3 equiv) was added dropwise such that the temperature remained below 20° C. After the addition the layers were separated, and the organic solution was dried (Na2SO4) and concentrated to afford 2.60 g of crude product. Analysis of this material by 1H NMR and GC indicated that the major product was 6 with 2 and 3 as minor products. 6: 1H NMR (CDCl3) δ 8.127 (d, 1H, J=1.8 Hz); 7.803 (dd, 1 H, J=2.1, 8.7 Hz); 7.203 (d, 1H, J=9.06 Hz); 4.028 (s, 3H). GC (30 m DB-17, 100° C., 3 min; 100-280° C., 15°/min); 280° C., 1 min): tR 9.35 min.

후처리

  1. temperaturecooled in a cool water bath
  2. additionadded slowly dropwise
  3. temperaturewith cooling such that the temperature
  4. customremained between 15 and 20° C
  5. additionAfter the addition
  6. customto completely consume 1 according to GC analysis
  7. additionToluene (10 mL) was added
  8. temperaturethe mixture was cooled in ice water
  9. customremained below 20° C
  10. additionAfter the addition the layers
  11. customwere separated
  12. dry with materialthe organic solution was dried (Na2SO4)
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-693d827bc00843c19116f1983e7c0f4d
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100431

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