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

HRID 1619700Notes

Reaction equation

HRID 1619700 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-36f9ba5dc32a49219546082825a47ee2
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…