Sulfuric Acid → 6-Chloro-3'-fluoro-4-iodobiphenyl-3-ol

HRID 1619700노트

반응식

HRID 1619700 반응식
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:14][C:13]([OH:23])=[CH:12][CH:11]=1.S(=O)(=O)(O)O>C(O)(=O)C.ClCCl>[Cl:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:14][C:13]([OH:23])=[C:12]([I:1])[CH:11]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 580422636-Chloro-3'-fluorobiphenyl-3-ol

생성물 1

HCID 580423086-Chloro-3'-fluoro-4-iodobiphenyl-3-ol수율 47.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

실험 절차

N-Iodosuccinimide (261 mg, 1.16 mmol) was added to a mixture of 6-chloro-3′-fluorobiphenyl-3-ol (Preparation 100, 270 mg, 1.21 mmol) and concentrated sulphuric acid (24 μL, 0.43 mmol) in acetic acid (3 mL) and dichloromethane (3 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with dichloromethane (10 mL) and washed with sodium metabisulfite (0.5M, 10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with heptane:dichloromethane (70:30) to give the title compound (193 mg, 46%) as a pale yellow solid.

후처리

  1. washwashed with sodium metabisulfite (0.5M, 10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with heptane:dichloromethane (70:30)

출처 및 근거

ORD 기록
ord-36f9ba5dc32a49219546082825a47ee2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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