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

HRID 1665240ノート

反応式

HRID 1665240 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-dc31e9fad0954bdd9855b18550548ea6
出典データセット
uspto-grants-2011_10
特許番号
US08039495B2

反応ノート

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