Triethylamine → 6-(Trifluoromethyl)isobenzofuran-1(3H)-one

HRID 452993Notes

Reaction equation

HRID 452993 reaction equation
OC[C:3]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[C]=O>CO.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:9]=[C:4]2[C:3]([CH2:8][O:7][C:5]2=[O:6])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66698240Methyl 2-(hydroxymethyl)-5-(trifluoromethyl)benzoateHCID 178418416HCID 178418416, compound

Product 1

HCID 110744416-(Trifluoromethyl)isobenzofuran-1(3H)-oneYield 63%

Reagents, catalysts & solvents 2

HCID 178506421HCID 178506421, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

Methyl 2-(hydroxymethyl)-5-(trifluoromethyl)benzoate (5.00 g, 21.4 mmol) in MeOH (50 mL) was added to Pd-dppf (Heraeus) (0.312 g, 0.427 mmol) and triethylamine (5.95 ml, 42.7 mmol) in a 250 mL stainless steel pressure bottle. The mixture was pressurized with carbon monoxide (60 psi), and stirred at 95° C. for 6 hours. The mixture was filtered through Celite, and the filtrate concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound (2.5 g, 63%). MS (DCI/NH3) m/z 203 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-67265e2459b14e46bfc1e88b683c1be7
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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