Water → 3-Iodo-3'-(trifluoromethyl)biphenyl-4-ol

HRID 1619622Notes

Reaction equation

HRID 1619622 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[I:18]N1C(=O)CCC1=O.O>C(O)(=O)C>[I:18][C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=2)[CH:14]=[CH:13][C:12]=1[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 200995974-(3-Trifluoromethylphenyl)phenol

Product 1

HCID 580422843-Iodo-3'-(trifluoromethyl)biphenyl-4-olYield 39.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3′-(trifluoromethyl)biphenyl-4-ol (Preparation 1, 2.17 g, 9.11 mmol) in acetic acid (20 mL) at 0° C. was added N-iodosuccinimide (2.05 g, 9.11 mmol). The reaction was allowed to warm to room temperature and stirred for 48 hours before the addition of water (20 mL). The reaction mixture was extracted with dichloromethane (2×20 mL) and the combined extracts were washed with saturated aqueous sodium thiosulfate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution) to afford the title compound (1.30 g, 39%).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (2×20 mL)
  2. washthe combined extracts were washed with saturated aqueous sodium thiosulfate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution)

Sources & evidence

ORD record
ord-e79e6675d1bb47ee9f6ca1128ea2c540
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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