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

HRID 880978

Reaction equation

HRID 880978 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-ee193e9496d840c59f80c6807398e0c3
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Linked notes

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