Ethanol → Benzoic acid, 2-fluoro-5-(trifluoromethyl)-, ethyl ester

HRID 76303ノート

反応式

HRID 76303 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(CC)CC.[CH3:22][CH2:23][OH:24]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([O:24][CH2:23][CH3:22])=[O:5]

参加物

5

反応物 3

HCID 702EthanolHCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl Chloride

生成物 1

HCID 46311387Benzoic acid, 2-fluoro-5-(trifluoromethyl)-, ethyl ester収率 92.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-fluoro-5-(trifluoromethyl)benzoyl chloride (5.0 g, 22.0 mmol) in THF (25 mL) was added Et3N (3.1 mL, 22.0 mmol) followed by EtOH (1.3 mL, 22.0 mmol). This mixture was stirred at ambient temperature for 1 h and quenched with saturated, aqueous NH4Cl (10 mL). The layers were separated and the aqueous layer was extracted with 3×10 mL EtOAc and the combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc) to give the title compound (4.8 g, 20.3 mmol, 92% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.42 (t, J=7.1 Hz, 3 H), 4.43 (q, J=7.1 Hz, 2 H), 7.23-7.34 (m, 1 H), 7.74-7.82 (m, 1 H), 8.23 (dd, J=6.3, 2.4 Hz, 1 H).

後処理

  1. customquenched with saturated, aqueous NH4Cl (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 3×10 mL EtOAc
  4. dry with materialthe combined organics were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography (SiO2, 60% hexanes in EtOAc)

出典と根拠

ORDレコード
ord-6ad123aa98ca491fb1847e6548bd8c08
出典データセット
uspto-grants-2014_09
特許番号
US08835475B2

反応ノート

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