Methyl chlorodifluoroacetate → HCID 57949698, compound

HRID 2427685Notes

Reaction equation

HRID 2427685 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]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH2:7]2.COC(=O)[C:27](Cl)([F:29])[F:28]>CN(C=O)C.[Cu]I>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([C:27]([F:29])([F:1])[F:28])[CH:12]=1)[C:9](=[O:14])[N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 67252295HCID 67252295, compound

Product 1

HCID 57949698HCID 57949698, compoundYield 50%

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 (0.055 g, 0.29 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-(4-methoxy-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.100 g, 0.24 mmol) and chloro-difluoro-acetic acid methyl ester (0.031 mL, 0.29 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-methoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.042 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.79 (s, 3H), 4.25 (s, 2H), 4.72 (s, 2H) 6.86 (d, 2H), 7.25 (d, 2H), 7.56 (s, 1H), 7.73 (s, 1H). GC-MS: m/z 355 (M)+, 334 (M−21)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-f647c0833f2f4d468b56171ce8aa67cb
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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