N-Iodosuccinimide → 6-Chloro-4'-fluoro-4-iodobiphenyl-3-ol

HRID 1619704Notes

Reaction equation

HRID 1619704 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][C:5]([OH:15])=[CH:4][CH:3]=1.[I:16]N1C(=O)CCC1=O>C(O)(=O)C.ClCCl.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][C:5]([OH:15])=[C:4]([I:16])[CH:3]=1

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 580423356-Chloro-4'-fluorobiphenyl-3-ol

Product 1

HCID 580423526-Chloro-4'-fluoro-4-iodobiphenyl-3-olYield 72.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-chloro-4′-fluorobiphenyl-3-ol (Preparation 104, 280 mg, 1.26 mmol) in acetic acid (2.5 mL), dichloromethane (2.5 mL) and concentrated sulfuric acid (25 μL) was added N-iodosuccinimide (272 mg, 1.21 mmol) at room temperature. The reaction mixture was stirred for 18 hours at room temperature. Dichloromethane (60 mL) was added and the organic layer was washed with brine (2×20 mL), dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography eluting 33% dichloromethane in heptane to afford the title compound (306 mg, 70%) as a colourless oil.

Workup

  1. washthe organic layer was washed with brine (2×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting 33% dichloromethane in heptane

Sources & evidence

ORD record
ord-4f3c67bb21404cebbf74b251aa3201e6
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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