Water → HCID 58042325, compound

HRID 1619677Notes

Reaction equation

HRID 1619677 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.S(=O)(=O)(O)O.[I:21]N1C(=O)CCC1=O.O>ClCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([I:21])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 120273N-Iodosuccinimide2×HCID 46314341HCID 46314341, compound

Product 1

HCID 58042325HCID 58042325, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-3′-fluorobiphenyl-4-ol (Preparation 69, 500 mg, 2.25 mmol) was dissolved in dichloromethane (5 mL) and acetic acid (5 mL). Concentrated sulfuric acid (0.05 mL) was added followed by N-iodosuccinimide (480 mg, 2.13 mmol) and the reaction stirred at room temperature for 18 hours. A further portion of N-iodosuccinimide (50 mg, 0.22 mmol) was added and stirring continued at room temperature for 3 hours. Water and dichloromethane were added and the two layers separated. The organic layer was washed twice with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (20% ethyl acetate in heptane) to afford the title compound (496 mg, 63%) as a yellow oil that solidified on standing.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 3 hours
  3. customthe two layers separated
  4. washThe organic layer was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-31d823c692eb46edb612248c227826d3
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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