Potassium Iodide → 4-Iodo-3-(trifluoromethyl)benzoic acid

HRID 2261807Notes

Reaction equation

N[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].N([O-])=O.[Na+].[I-:19].[K+]>Cl.O>[I:19][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

Conditions

Temperature: 5 °C

Procedure

To a 0° C. suspension of 4-Amino-3-trifluoromethyl benzoic acid (1.8 g, 8.8 mmol) in conc. HCl (30.0 mL) is added a solution of sodium nitrite (0.76 g, 11.0 mmol) in water (15 mL) dropwise. The mixture is stirred at 0-10° C. for 30 min. A solution of potassium iodide (14.6 g, 88 mmol) in water (25 mL) is added dropwise. The mixture is stirred at room temperature for 1.0 h. The reaction mixture is extracted with EtOAc (80 mL), washed with brine (80 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as solid (2.4 g, 86%). LC-ES/MS: 339.3 (M+23), 315.0 (M−1).

Workup

stirringThe mixture is stirred at room temperature for 1.0 h
extractionThe reaction mixture is extracted with EtOAc (80 mL)
washwashed with brine (80 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure to a residue
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-73b2c489075c41048e8ab5f0df62d51d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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