Methyl chlorodifluoroacetate → HCID 57949628, compound

HRID 2427684Notes

Reaction equation

HRID 2427684 reaction equation
[F-:1].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11](I)[CH:12]=1)[C:9](=[O:14])[N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:7]2.COC(=O)[C:26](Cl)([F:28])[F:27]>CN(C=O)C.[Cu]I>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:26]([F:28])([F:1])[F:27])[CH:12]=1)[C:9](=[O:14])[N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 67252468HCID 67252468, compound

Product 1

HCID 57949628HCID 57949628, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

CuI (0.076 g, 0.4 mmol) and potassium fluoride (0.023 g, 0.4 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-(4-fluoro-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.149 g, 0.37 mmol) and chloro-difluoro-acetic acid methyl ester (0.046 mL, 0.43 mmol) in DMF (4 mL). The mixture was stirred at 140° C. for 18 h. The reaction was cooled and the solvent evaporated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-chloro-2-(4-fluoro-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.025 g, 20%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.37 (s, 2H), 4.76 (s, 2H) 7.05 (m, 2H), 7.26 (m, 2H), 7.56 (s, 1H), 7.78 (s, 1H). GC-MS: m/z 343 (M)+, 322 (M−21)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-8176930c4333495594435fe2e54fdcc7
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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