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

HRID 478276노트

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HRID 478276 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 23497488(4-Fluoro-3-iodophenyl)methanol수율 50.8%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fc2f1b35e69d40289770d2d62c562cb3
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642222B2

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