2-Bromo-3'-chloroacetophenone → Phthalimide

HRID 1466567Notes

Reaction equation

HRID 1466567 reaction equation
BrCC(C1C=CC=C(Cl)C=1)=O.[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)C=O>[C:15]1(=[O:17])[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:22])[NH:16]1

Participants

4

Reactant 2

HCID 387382-Bromo-3'-chloroacetophenoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-bromo-3′-chloroacetophenone (0.927 g, 3.97 mmol, 1 eq) and potassium phthalimide (0.813 g, 4.39 mmol, 1.1 eq) in 15 mL N,N-dimethylformamide was stirred at 50° C. for one hour. The solvent was removed under vacuum. The resulting solids were triturated with ethyl acetate and filtered. The collected solids were dried under vacuum to give 24243-chlorophenyl)-2-oxoethyl)isoindoline-1,3-dione, which was carried forward without purification. 1H NMR (400 MHz, DMSO-d6) δ: 8.13 (s, 1H), 8.05 (d, 1H), 7.96 (m, 2H), 7.93 (m, 2H), 7.83 (d, 1H), 7.65 (t, 1H), 5.29 (s, 2H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe resulting solids were triturated with ethyl acetate
  3. filtrationfiltered
  4. customThe collected solids were dried under vacuum

Sources & evidence

ORD record
ord-56c89b5a4acf4d46a540c247aa342b2f
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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