Ethanol → Ethyl 5-methoxy-2,3,4-trifluorobenzoate

HRID 729364노트

반응식

HRID 729364 반응식
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](Cl)(=O)[C:16](Cl)=O.C(O)C.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C=O>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([O:13][CH3:14])[C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[CH3:16]

참가 물질

7

반응물 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 219792035-Methoxy-2,3,4-trifluorobenzoic acid

생성물 1

HCID 21041176Ethyl 5-methoxy-2,3,4-trifluorobenzoate수율 96.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 2,3,4-trifluoro-5-methoxybenzoic acid (Hayashi et al., Bull. Chem. Soc. Jap., 1972; 45(9):2909-2914, 3.443 g, 16.7 mmol) in dichloromethane (100 mL) at 0° C. is treated with oxalyl chloride (7 mL, 80 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at room temperature for 3.5 hours, concentrated to near dryness, and co-evaporated with benzene. The acid chloride is then diluted with dichloromethane, cooled to 0° C., and treated with absolute ethanol (10 mL, 170 mmol). The resulting solution is stirred at room temperature for 20 hours, poured into saturated NaHCO3 solution, and extracted with dichloromethane. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to afford the title compound (3.785 g). 1H NMR (200 MHz, CDCl3): δ 7.36-7.29 (m, 1H), 4.42 (q, 2H), 3.93 (s, 3H), 1.44 (t, 3H).

후처리

  1. concentrationconcentrated
  2. additionThe acid chloride is then diluted with dichloromethane
  3. temperaturecooled to 0° C.
  4. stirringThe resulting solution is stirred at room temperature for 20 hours
  5. extractionextracted with dichloromethane
  6. washThe organic extracts are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-29e53bcfcca947d8accf2d883a0e3c94
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

반응 노트

불러오는 중…