Chloroform → HCID 7571580, compound

HRID 2298172Notes

Reaction equation

HRID 2298172 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].C(Cl)(Cl)Cl>CN(C=O)C>[Cl:12][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([Cl:11])[CH:8]=1)[O:4][CH2:3][CH2:2][N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 222467761-(2-Bromoethoxy)-3,5-dichlorobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 7571580HCID 7571580, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-bromo-ethoxy)-3,5-dichloro-benzene (2.41 g, 8.93 mmol) and potassium phthalimide (2.00 g, 10.64 mmol) in DMF (7.6 mL) was heated at 85° C. for 1 h. The reaction was cooled to room temperature and chloroform was added. The organic solution was washed with 0.2 N aqueous NaOH followed by water. The organic solution was dried (Na2SO4), filtered, and concentrated. The residue was suspended in Et2O and the solid was collected by filtration to provide the title compound (2.21 g). 1HNMR (400 MHz, CDCl3) δ 7.82 (m, 2H), 7.77 (m, 2H), 6.89 (m, 1H), 6.88 (m, 2H), 4.16 (t, 2H), 4.05 (t, 2H); MS 336 (M+).

Workup

  1. washThe organic solution was washed with 0.2 N aqueous NaOH
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-019727161bed4bc9bce30c8c1dde2255
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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