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

HRID 10274

反応式

HRID 10274 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1ce2e721306346368ed59e7d64aa7c46
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

関連ノート

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