Water → 4-Fluoro-2-(phenylamino)benzoic acid

HRID 1887825노트

반응식

HRID 1887825 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4](Br)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(OCCO)C.[Cu].[Cu]I>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 6115AnilineHCID 11430Potassium CarbonateHCID 12681692-Bromo-4-fluorobenzoic acid

생성물 1

HCID 217338394-Fluoro-2-(phenylamino)benzoic acid

시약·촉매·용매 3

HCID 23978Copper촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8076Glycol monoethyl ether용매

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온도
138 °C

실험 절차

A mixture of 4-fluoro-2-bromo-benzoic acid (25 g, 114 mmol), aniline (12.5 mL, 137 mmol), potassium carbonate (17.4 g, 126 mmol), copper powder (725 mg, 11.4 mmol), and copper (I) iodide (1.09 g, 5.71 mmol) in 2-ethoxyethanol (70 mL) was stirred at 138° C. for 70 hr. under an argon atmosphere. The reaction mixture was cooled to room temperature, then water (60 mL) was added. The mixture was filtered through celite. The filtrate was adjusted to pH<2, then an additional 200 mL of water was added. The mixture was allowed to stir for 1 hr. The precipitated solids were collected via filtrated. The solids were taken up into 5% sodium carbonate solution, then filtered. The product was dried under vacuum overnight at 85° C.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered through celite
  3. additionan additional 200 mL of water was added
  4. stirringto stir for 1 hr
  5. customThe precipitated solids were collected
  6. filtrationvia filtrated
  7. filtrationfiltered
  8. customThe product was dried under vacuum overnight at 85° C.

출처 및 근거

ORD 기록
ord-98ef912781b14a6882a0d75ea82ec416
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501732B2

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