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

HRID 10275ノート

反応式

HRID 10275 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-49a5979b87634687b079fe6f0767adec
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

反応ノート

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