Hydrochloric Acid → 4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid

HRID 389980ノート

反応式

HRID 389980 の反応式
[CH2:1]([C:3]1[C:18]([F:19])=[CH:17][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#N)=[CH:10][C:9]=2[F:16])=[C:5]([O:20][CH3:21])[CH:4]=1)[CH3:2].[OH-:22].[Na+].Cl.C[OH:26]>C(OCC)(=O)C.O>[CH2:1]([C:3]1[C:18]([F:19])=[CH:17][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]([OH:26])=[O:22])=[CH:10][C:9]=2[F:16])=[C:5]([O:20][CH3:21])[CH:4]=1)[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 510347494-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzonitrile

生成物 1

HCID 671160464-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzonitrile (420 mg, 1.45 mmol; which may be prepared as described in D1) in methanol (15 mL) was added an aqueous solution of 6N NaOH (7.3 mL, 43.6 mmol). The reaction mixture was heated to reflux (70° C.) and stirred overnight. After cooling with an ice bath, concentrated HCl (3.7 mL) was added slowly. The mixture was diluted with ethyl acetate and water. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtrated and concentrated in vacuo to give the title product as a beige solid (447 mg, quantitative).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureAfter cooling with an ice bath
  3. customThe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-43917f089607415b870b5794e7fc185c
出典データセット
uspto-grants-2013_02
特許番号
US08383621B2

反応ノート

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