Hydrochloric Acid → 2-Fluoro-4-phenylbenzoic acid

HRID 2053694노트

반응식

HRID 2053694 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]=1[F:17])=[O:4].[OH-].[Na+].Cl>C1COCC1>[F:17][C:6]1[CH:7]=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69129634Methyl 2-fluoro-4-phenylbenzoate

생성물 1

HCID 113902902-Fluoro-4-phenylbenzoic acid수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Combine methyl 2-fluoro-4-bromobenzoate (1.25 g, 5.36 mmol), phenylboronic acid (1.30 g, 10.72 mmol) and CsF (2.02 g, 13.40 mmol) in DMF (25 mL) and water (3.0 mL) with stirring. Place the hetereogeneous reaction mixture open to the air in an oil bath maintained at 80° C. After 5 minutes of heating, add Pd(OAc)2 (120 mg, 0.536 mmol) in one portion and stir until reaction turns black. Cool reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash organics with water, dry over MgSO4, filter and evaporate. Purification by flash column chromatography yields 3-fluorobiphenyl-4-carboxylic acid methyl ester as a solid. Dissolve the purified ester in THF (0.25M) and add an equal volume of 1 M NaOH. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCl and extract with ethyl acetate. Evaporation of the solvent yields 965 mg (84%) of the title compound. MS (m/e): 214.9 (M−).

후처리

  1. extractionextract with ethyl acetate
  2. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-5ac562ed753d48799069e9230ea9f11b
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326731B2

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