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

HRID 537172

Reaction equation

HRID 537172 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-89405abb30dc4596aa617a820cba13eb
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Linked notes

Loading…