2-Bromo-3'-chloroacetophenone → 2-(2-(3-Chlorophenyl)-2-oxoethyl)isoindoline-1,3-dione

HRID 474336Notes

Reaction equation

HRID 474336 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[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)C=O>[Cl:11][C:7]1[CH:6]=[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:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

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

Product 1

HCID 580630902-(2-(3-Chlorophenyl)-2-oxoethyl)isoindoline-1,3-dioneYield 117%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-3′-chloroacetophenone (0.9271 g, 3.971 mmol, 1.0 equiv) and potassium phthalimide (0.8129 g, 4.389 mmol, 1.1 equiv) in N,N-dimethylformamide (15 mL) was heated at 50° C. After 1 hour, the solvent was removed by rotary evaporation. The resultant solids were triturated with ethyl acetate and filtered. The collected solids were dried under vacuum to yield 1.19 g (117%) of 2-(2-(3-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 by rotary evaporation
  2. customThe resultant solids were triturated with ethyl acetate
  3. filtrationfiltered
  4. customThe collected solids were dried under vacuum

Sources & evidence

ORD record
ord-211a0d6c456b45bd97c7afc8cfc622e5
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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