Phthalimide → HCID 17755957, compound

HRID 2382551Notes

Reaction equation

HRID 2382551 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromide

Product 1

HCID 17755957HCID 17755957, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-benzyl bromide (9.04 g, 30.4 mmol) in DMF (316 mL) was added phthalimide (4.47 g, 30.4 mmol) and cesium carbonate (14.86 g, 45.6 mmol). The reaction stirred at room temperature overnight under nitrogen atmosphere. The next day, the reaction mixture was quenched with water. The product precipitated from the quenched reaction mixture and was filtered off, washed with water, and collected as a white solid (9.5 g, 86% yield). 1H NMR (600 MHz, CDCl3): δ 7.84 (m, 2H), 7.71 (m, 2H), 7.63 (d, 2H, J=8.4 Hz), 7.17 (d, 2H, J=8.4 Hz), 4.77 (s, 2H). 13C NMR (150 MHz, CDCl3): δ 168.1, 138.0, 136.2, 134.3, 132.2, 130.8, 123.6, 93.7, 41.3.

Workup

  1. customThe next day, the reaction mixture was quenched with water
  2. customThe product precipitated from the quenched reaction mixture
  3. filtrationwas filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-ea13bbcb7bb54771b32b50206251e416
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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