Dichloromethane → HCID 86635683, compound

HRID 2427766Notes

Reaction equation

HRID 2427766 reaction equation
I[C:2]1[CH:3]=[C:4]([O:24][CH:25]([F:27])[F:26])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[Cl:28]CCl>CN(C=O)C.Cl[Cu]>[Cl:28][C:2]1[CH:3]=[C:4]([O:24][CH:25]([F:27])[F:26])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67252112HCID 67252112, compound

Product 1

HCID 86635683HCID 86635683, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of the 7-iodo-5-difluoromethoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindolone (0.082 g, 0.16 mmol) in DMF (5 mL) was treated with CuCl (0.064 g, 0.65 mmol) and stirred at 140° C. for 1-2 h. After this time, the reaction mixture was diluted with dichloromethane (15 mL) and the solids removed by filtration. The filtrate was concentrated. Silica gel column chromatography using, typically 30% ethyl acetate in hexane, afforded 7-Chloro-2-(4-trifluoromethoxy-benzyl)-5-difluoromethoxy-2,3-dihydro-isoindolone (0.02 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.08 (s, 2H), 4.58 (s, 2H), 6.37 (t, 1H), 6.87 (s, 1H), 7.01 (m, 3H), 7.17 (d, 2H). GC-MS: m/z 407 (M)+, 322 (M−85)+.

Workup

  1. customthe solids removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-51d5e1c3a01849aeaf85cf6495cb33b5
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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