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

HRID 389980노트

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HRID 389980 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-43917f089607415b870b5794e7fc185c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383621B2

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