Ethanol → Benzoic acid, 2,4,5-trifluoro-3-methoxy-, ethyl ester

HRID 10273ノート

反応式

HRID 10273 の反応式
[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[C:8]([F: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]([F:14])[C:9]([F:13])=[C:10]([O:11][CH3:12])[C:2]=1[F:1])[CH3:16]

参加物

7

反応物 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 27339702,4,5-Trifluoro-3-methoxybenzoic acid

生成物 1

HCID 2774387Benzoic acid, 2,4,5-trifluoro-3-methoxy-, ethyl ester収率 98.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 2,4,5-trifluoro-3-methoxybenzoic acid (2.513 g, 12.19 mmol) in dichloromethane (50 mL) at 0° C. is treated with oxalyl chloride (5.4 mL, 61.9 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at 0° C. for 5 minutes and then at room temperature for 2.5 hours. The mixture is concentrated to near dryness and then co-evaporated from benzene. The resulting acid chloride is diluted with dichloromethane (50 mL), cooled to 0° C., and then anhydrous ethanol (7.30 mL, 124 mmol) is added dropwise. The resulting solution is stirred at room temperature for 4.5 hours, poured into saturated NaHCO3 solution, and extracted with dichloromethane. The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to afford the title compound as a light yellow liquid (2.82 g). 1H NMR (CDCl3): δ 7.47 (ddd, 1H), 4.39 (q, 2H), 4.05 (s, 3H), 1.40 (t, 3H).

後処理

  1. waitat room temperature for 2.5 hours
  2. concentrationThe mixture is concentrated
  3. additionThe resulting acid chloride is diluted with dichloromethane (50 mL)
  4. temperaturecooled to 0° C.
  5. stirringThe resulting solution is stirred at room temperature for 4.5 hours
  6. extractionextracted with dichloromethane
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-773f119220524fabb53ac3ee22baac20
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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