2-Bromo-1-(4-iodophenyl)ethanone → HCID 8220607, compound

HRID 1256210Notes

Reaction equation

HRID 1256210 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)=[O:4].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C=O)C>[I:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2565722-Bromo-1-(4-iodophenyl)ethanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 8220607HCID 8220607, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 ml round-bottomed flask is charged with 66 g of 2-bromo-1-(4-iodophenyl)ethanone in 140 ml of DMF and 38 g of potassium phthalimide. The mixture is stirred at RT for 4 h and the precipitate formed is filtered off on a glass frit and washed with 3 times 50 ml of isopropyl ether. Drying under RP gives 80 g of 2-[2-(4-iodophenyl)-2-oxoethyl]isoindole-1,3-dione in the form of a white solid, which is used as it is in the following step. MS (E/I): m/z=391 (M+); 1H NMR: 5.21 (s, 2H); 7.84 (d, J=8.5 Hz, 2H); from 7.88 to 7.98 (m, 4H); 8.00 (d, J=8.5 Hz, 2H). m.p. (Kofler): 230° C.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off on a glass frit
  3. washwashed with 3 times 50 ml of isopropyl ether
  4. customDrying under RP

Sources & evidence

ORD record
ord-5a4a611ad051403593a1279f190771e9
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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