Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol

HRID 478276ノート

反応式

HRID 478276 の反応式
N[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][OH:6].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:20].[K+]>O>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[I:20]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 13563644(3-Amino-4-fluorophenyl)methanolHCID 23668193Sodium Nitrite

生成物 1

HCID 23497488(4-Fluoro-3-iodophenyl)methanol収率 50.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
60 °C

実験手順

The product from Example 30A (7.0 g, 50 mmol) in water (100 mL) at 0° C. was treated slowly with concentrated sulfuric acid (30 mL) at a rate to maintain the temperature below 10° C. and then treated dropwise with an aqueous solution of sodium nitrite (3.45 g, 50 mmol). This solution was then added to a solution of potassium iodide (8.13 g, 50 mmol) in water (15 mL), heated to 60° C. for 2 hours, cooled and extracted with methylene chloride. The methylene chloride layer was washed with 10% sodium hydroxide, washed with 1M sodium thiosulfate, washed with 10% hydrochloric acid, washed with aqueous sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3) to provide 6.4 g of the title compound.

後処理

  1. temperatureto maintain the temperature below 10° C.
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer was washed with 10% sodium hydroxide
  5. washwashed with 1M sodium thiosulfate
  6. washwashed with 10% hydrochloric acid
  7. washwashed with aqueous sodium bicarbonate
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)

出典と根拠

ORDレコード
ord-fc2f1b35e69d40289770d2d62c562cb3
出典データセット
uspto-grants-2003_11
特許番号
US06642222B2

反応ノート

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