Methyl chlorodifluoroacetate → HCID 67251332, compound

HRID 2427686Notes

Reaction equation

HRID 2427686 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]([CH:15]1[CH2:17][CH2:16]1)[CH:7]2[CH3:18].COC(=O)[C:22](Cl)([F:24])[F:23]>CN(C=O)C.[Cu]I>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:22]([F:24])([F:1])[F:23])[CH:12]=1)[C:9](=[O:14])[N:8]([CH:15]1[CH2:17][CH2:16]1)[CH:7]2[CH3:18]

Participants

6

Reactant 3

HCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 67252349HCID 67252349, compound

Product 1

HCID 67251332HCID 67251332, 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 (0.080 g, 0.42 mmol) and potassium fluoride (0.024 g, 0.42 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-cyclopropyl methyl-7-iodo-2,3-dihydro-isoindol-1-one (0.123 g, 0.35 mmol) and chloro-difluoro-acetic acid methyl ester (0.046 mL, 0.42 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-cyclopropyl methyl-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.020 g, 20%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.33 (s, 2H), 0.59 (m, 2H), 1.05 (m, 1H), 3.48 (d, 2H) 4.53 (s, 2H), 7.64 (s, 1H), 7.73 (s, 1H). GC-MS: m/z 289 (M)+, 274 (M-15)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-0c1559495aa1400d854e8ff872ab927b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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