Dichloromethane → HCID 67251981, compound

HRID 2427767Notes

Reaction equation

HRID 2427767 reaction equation
I[C:2]1[CH:3]=[C:4]([O:21][CH:22]([F:24])[F:23])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH3:13])[CH2:7]2.[Cl:25]CCl>CN(C=O)C.Cl[Cu]>[Cl:25][C:2]1[CH:3]=[C:4]([O:21][CH:22]([F:24])[F:23])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH3:13])[CH2:7]2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67252015HCID 67252015, compound

Product 1

HCID 67251981HCID 67251981, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of the 7-iodo-2-[1-(4-chloro-phenyl)-ethyl]-5-difluoromethoxy-2,3-dihydro-isoindolone (0.122 g, 0.26 mmol) in DMF (5 mL) was treated with CuCl (0.130 g, 1.31 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-[1-(4-chloro-phenyl)-ethyl]-5-difluoromethoxy-2,3-dihydro-isoindolone (0.05 g, 52%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.66 (d, 3H), 3.94 (d, 1H), 4.27 (d, 1H), 5.74 (q, 1H), 6.54 (t, 1H), 7.17 (s, 1H), 7.26 (s, 1H), 7.31 (m, 4H). GC-MS: m/z 371 (M)+, 356 (M−15)+.

Workup

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

Sources & evidence

ORD record
ord-bc2ec0550547459aac15551190dd97a2
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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