Hydrochloric Acid → 2,4-Difluoro-6-iodophenol

HRID 1468469ノート

反応式

HRID 1468469 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Na+].[I-:11].[OH-].[Na+].[O-]Cl.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([I:11])[C:3]=1[OH:9]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 1230512,4-DifluorophenolHCID 23665760Sodium Hypochlorite

生成物 1

HCID 222216242,4-Difluoro-6-iodophenol収率 41.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 10 g of 2,4-difluorophenol in 300 mL of methanol at 0° C., add 22.5 g (150.2 millimoles (mmol) of NaI and 3.08 g (77 mmol) of NaOH. To the resulting mixture add 175 mL of 5% aqueous NaOCl solution (commercial bleach) over a one hour period. Stir the resulting slurry for one more hour at 0° C. Add 100 mL of 10% aqueous Na2S2O3 solution, and acidify the resulting reaction mixture by adding dilute hydrochloric acid. Extract the resulting mixture with methylene chloride, wash the resulting organic layer with brine and dry it over anhydrous magnesium sulfate. Remove solvent and purify the residue by flash chromatography using 50 vol % methylene chloride in hexanes to yield 8.10 g (41.16%) of pure 2,4-difluoro-6-iodophenol (P7) as a white solid.

後処理

  1. customthe resulting reaction mixture
  2. extractionExtract the resulting mixture with methylene chloride
  3. washwash the resulting organic layer with brine
  4. dry with materialdry it over anhydrous magnesium sulfate
  5. customRemove solvent and purify the residue by flash chromatography

出典と根拠

ORDレコード
ord-7e8ac803fabd4fcb89fa28609e4f0dd6
出典データセット
uspto-grants-2015_04
特許番号
US09000108B2

反応ノート

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