Methyl chlorodifluoroacetate → HCID 57949784, compound

HRID 2427638Notes

Reaction equation

HRID 2427638 reaction equation
[F-:1].[K+].[CH2:3]([N:10]1[CH2:18][C:17]2[C:12](=[C:13](I)[CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COC(=O)[C:24](Cl)([F:26])[F:25]>CN(C=O)C.[Cu]I>[CH2:3]([N:10]1[CH2:18][C:17]2[C:12](=[C:13]([C:24]([F:26])([F:1])[F:25])[CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 57949681HCID 57949681, compound

Product 1

HCID 57949784HCID 57949784, compoundYield 41.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

CuI (0.057 g, 0.3 mmol) and potassium fluoride (0.017 g, 0.3 mmol) were added under N2 atmosphere to a stirred solution of 2-benzyl-7-iodo-2,3-dihydro-isoindol-1-one (0.089 g, 0.25 mmol) and chloro-difluoro-acetic acid methyl ester (0.053 mL, 0.5 mmol) in DMF (3 mL). The mixture was heated at 140° C. for 5-8 h. The reaction was cooled and the solvent evaporated. Silica gel column chromatography of the resulting material using 30% ethyl acetate in hexane afforded 2-benzyl-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.03 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.79 (s, 2H), 7.33 (m, 5H), 7.59 (m, 2H), 7.76 (d, 1H). GC-MS: m/z 291 (M)+, 270 (M−20)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-b33f761854834b59937732171704034b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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