Sulfuric Acid → 2-Chloro-4'-fluoro-5-iodobiphenyl-4-ol

HRID 1619681Notes

Reaction equation

HRID 1619681 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][C:12]([F:15])=[CH:11][CH:10]=1.S(=O)(=O)(O)O.[I:21]N1C(=O)CCC1=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][C:12]([F:15])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 463143422-Chloro-4'-fluorobiphenyl-4-ol

Product 1

HCID 580423282-Chloro-4'-fluoro-5-iodobiphenyl-4-olYield 70.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4′-fluorobiphenyl-4-ol (Preparation 73, 503 mg, 2.26 mmol) was dissolved in dichloromethane (5 mL) and acetic acid (5 mL). Concentrated sulfuric acid (0.05 mL) was added followed by N-iodosuccinimide (508 mg, 2.26 mmol) and the reaction stirred at room temperature for 2 hours before partitioning it between water and dichloromethane. The organic layer was separated and 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 (553 mg, 70%) as an orange oil.

Workup

  1. custombefore partitioning it between water and dichloromethane
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-e88929c5e07244138b71ceeb2bd139d9
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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