2-Iodoxybenzoic acid → 1-(2-Bromo-5-trifluoromethylphenyl)-ethanone

HRID 1473342Notes

Reaction equation

HRID 1473342 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH:12]([OH:14])[CH3:13].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 57458795HCID 57458795, compound

Product 1

HCID 574587961-(2-Bromo-5-trifluoromethylphenyl)-ethanoneYield 125.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound 1-(2-bromo-5-(trifluoromethyl)phenyl)ethanol (10.4 g, 44.6 mmol) in the dimethylsulfoxide (50 mL), 2-iodoxybenzoic acid (25 g, 89.2 mmol) at 0° C. The reaction was warmed to 25° C. and stirred at this temperature for 2 hours under a nitrogen atmosphere. Then the reaction mixture was diluted with water (500 mL), extracted with ethyl acetate (2×500 mL). Organic part was dried over sodium sulfate, filtered and concentrated under a vacuum to give the crude compound 1-(2-bromo-5-(trifluoromethyl)phenyl)ethanone (15 g), as a brown liquid. 1H NMR (400 MHz, DMSO) δ 8.03 (s, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 2.62 (s, 3H).

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate (2×500 mL)
  3. dry with materialOrganic part was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-ce3bfcca868c49a1a65c275e5ffc41b1
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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