Chloroform → HCID 7571580, compound

HRID 1699035Notes

Reaction equation

HRID 1699035 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) δ7.82 (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-40f8a1ad62634512a1dc184461b94d73
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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