Sulfuric Acid → HCID 58042312, compound

HRID 1619665Notes

Reaction equation

HRID 1619665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].S(=O)(=O)(O)O.[I:24]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([I:24])[CH:13]=2)=[CH:4][C:3]=1[C:15]([F:16])([F:17])[F:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 230050884′-Chloro-3′-(trifluoromethyl)[1,1′-biphenyl]-4-ol

Product 1

HCID 58042312HCID 58042312, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4′-Chloro-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 54, 150 mg, 0.55 mmol) was dissolved in acetic acid (5 mL) and concentrated sulphuric acid (0.032 μL) was added followed by N-iodosuccinimide (124 mg, 0.55 mmol). The reaction was stirred at room temperature for 18 hours and then partitioned between ethyl acetate (50 mL) and water (20 mL). The ethyl acetate was separated, dried over MgSO4, filtered and evaporated. The crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 85:15 to give the title compound (167 mg, 0.42 mmol, 76%) as a gum.

Workup

  1. custompartitioned between ethyl acetate (50 mL) and water (20 mL)
  2. customThe ethyl acetate was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 85:15

Sources & evidence

ORD record
ord-cb9d417d0775457a82722fcef911dce2
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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