Acetic Acid → HCID 58042353, compound

HRID 1619684Notes

Reaction equation

HRID 1619684 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]=[CH:11][C:10]=1[F:15].C(O)(=O)C.[I:20]N1C(=O)CCC1=O.S(=O)(=O)(O)O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([I:20])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 46314340HCID 46314340, compound

Product 1

HCID 58042353HCID 58042353, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-2′-fluorobiphenyl-4-ol (Preparation 76, 430 mg, 1.93 mmol) was dissolved in DCM, and cooled to 0° C. Acetic acid (5 mL), N-iodosuccinimide (434 mg, 1.93 mmol) were added followed by concentrated sulphuric acid (0.2 mL). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with heptane:ethyl acetate 7:3 to give the title compound (620 mg, 92%) as oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica gel eluting with heptane:ethyl acetate 7:3

Sources & evidence

ORD record
ord-fafa4764690441609d478f6a4adb336a
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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