Ethanol → Benzoic acid, 2,3,4-trifluoro-, ethyl ester

HRID 729363

반응식

HRID 729363 반응식
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)[C:14](Cl)=O.C(O)C>ClCCl.CN(C)C=O>[CH2:13]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[CH3:14]

참가 물질

6

반응물 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 3029322,3,4-Trifluorobenzoic acid

생성물 1

HCID 594559Benzoic acid, 2,3,4-trifluoro-, ethyl ester수율 97.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2,3,4-trifluorobenzoic acid (10.85 g, 61.6 mmol) in dichloromethane (100 mL) is added oxalyl chloride (13.5 mL, 154 mmol) and N,N-dimethylformamide (3 drops). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (100 mL) and to this solution is added ethanol (18 mL, 310 mmol). After 30 minutes, the reaction mixture is diluted with dichloromethane and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate is concentrated to afford the title compound as an oil (12.23 g). 1H NMR (CDCl3): δ 7.93-7.67 (m, 1H), 7.09-6.96 (m, 1H), 4.39 (q, 2H), 1.40 (t, 3H).

후처리

  1. concentrationthe reaction mixture is concentrated under vacuum
  2. dissolutionThe resulting residue is dissolved in dichloromethane (100 mL) and to this solution
  3. waitAfter 30 minutes
  4. washwashed with saturated NaHCO3, water, and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated

출처 및 근거

ORD 기록
ord-be480b588a864e4dbc2756db120f21fb
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

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