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

HRID 424812Notes

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

4-Amino-3-trifluoromethyl benzoic acid (1.8 g, 8.8 mmol) is suspended in conc. HCl (30 mL). A solution of sodium nitrite (0.76 g, 11.0 mmol) in water (15 mL) is added dropwise at 0° C. 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 h. The product 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 using a gradient (EtOAc/Hexane) to afford the title compound (2.4 g, 86%) as a solid. LC-ES/MS m/e 339.3 (M+23), 315.0 (M−1).

Workup

stirringThe mixture is stirred at room temperature for 1 h
extractionThe product 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-3fe50a40c24c46e4a2614e7bd205cada
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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