2-Iodoxybenzoic acid → 1-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

HRID 711093

Reaction equation

HRID 711093 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([F:14])[CH:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 616446351-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 669578641-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-oneYield 95.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromo-2-fluorophenyl)-2,2,2-trifluoroethanol (1.09 g, 3.99 mmol) in ethyl acetate (30 mL) was added 2-iodoxybenzoic acid (2.28 g, 7.97 mmol). The reaction was heated to reflux overnight. The reaction was cooled to room temperature and diluted with heptanes (30 mL). The mixture was filtered through Celite and the filtrate was concentrated to give the title compound (1.03 g, 95%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3, δ): 7.44 (dd, J=10.15, 1.56 Hz, 1H), 7.48 (m, 1H), 7.76 (m, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2640f2ca716a4496b7a81e253e79dbf7
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Linked notes

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