Isopropyl iodide → Isopropyl 2-formyl-6-(trifluoromethyl)benzoate

HRID 2100563Notes

Reaction equation

HRID 2100563 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:15])[O:3]1.C(=O)([O-])[O-].[K+].[K+].I[CH:23]([CH3:25])[CH3:24]>CN(C=O)C.Cl>[CH:2]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:5]=1[C:4]([O:3][CH:23]([CH3:25])[CH3:24])=[O:15])=[O:1]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 161151451(3H)-Isobenzofuranone, 3-hydroxy-7-(trifluoromethyl)-

Product 1

HCID 86090052Isopropyl 2-formyl-6-(trifluoromethyl)benzoateYield 87.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-3-hydroxy-7-(trifluoromethyl)isobenzofuran-1(3H)-one (2.2 g, 10.1 mmol) in 20 mL of DMF was added potassium carbonate (2.8 g, 20.2 mmol) followed by 2-iodopropane (1.11 mL, 11.1 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was diluted with 1N HCl to pH ˜4 and extracted with EtOAc. The organics were washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 2.3 g (87%) of the title compound which was used without purification. 1H NMR (CDCl3): δ 10.08 (s, 1H), 8.12 (d, 1H, J=7.7 Hz), 7.95 (d, 1H, J=8.2 Hz), 7.73 (t, 1H, J=7.7 Hz), 5.44-5.36 (m, 1H), 1.40 (d, 1H, J=6.6 Hz).

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with 1N HCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-174b227e9dd549848fc0a4b0cc621497
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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