4-Iodophenol → 4-Fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester

HRID 1665240노트

반응식

HRID 1665240 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11]Br)[CH:5]=1.[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11][O:21][C:18]2[CH:19]=[CH:20][C:15]([I:14])=[CH:16][CH:17]=2)[CH:5]=1

참가 물질

5

반응물 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 53419607Benzoic acid, 3-(bromomethyl)-4-fluoro-, methyl ester

생성물 1

HCID 671503534-Fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester수율 74.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

3-Bromomethyl-4-fluorobenzoic acid methyl ester (3.0 g, 12.1 mmol) was mixed with 4-iodophenol (3.2 g, 14.6 mmol) in acetone (75 mL) containing dry potassium carbonate (2.5 g, 18 mmol). The mixture was refluxed for 6 hrs and then filtered. The filtrate was concentrated and extracted with ether and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The residue was purified through flash column chromatography (120 g silica gel, 0% to 20% ethyl acetate in hexanes over 40 minutes) to give clear oil as 4-fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester (3.48 g, 74.4%).

후처리

  1. temperatureThe mixture was refluxed for 6 hrs
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with ether and water
  5. dry with materialThe organic layer was dried over sodium sulfate and solvents
  6. customwere evaporated
  7. customThe residue was purified through flash column chromatography (120 g silica gel, 0% to 20% ethyl acetate in hexanes over 40 minutes)

출처 및 근거

ORD 기록
ord-dc31e9fad0954bdd9855b18550548ea6
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039495B2

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