2-Bromo-1-(4-fluorophenyl)ethan-1-one → 2-[2-(4-fluorophenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

HRID 1256224Notes

Reaction equation

HRID 1256224 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][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=O)C>[F:11][C:8]1[CH:9]=[CH:10][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:6][CH:7]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 24194345Phthalimide potassium salt

Product 1

HCID 28152022-[2-(4-fluorophenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dioneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 50 ml round-bottomed flask equipped with a magnetic stirrer and with a septum having a top-mounted argon intake is charged with 4.2 g of 2-bromo-1-(4-fluorophenyl)ethanone in 10 ml of DMF and 3.6 g of potassium phthalimide. The mixture is stirred at RT for 4 h and the precipitate formed is filtered off on a glass frit and washed with 3 times 50 ml of isopropyl ether. This, after drying under RP, gives 5 g of 2-[2-(4-fluorophenyl)-2-oxoethyl]isoindole-1,3-dione (white solid), which is used as it is in the following step. Melting point (Kofler): 140° C.; MS (E/I): m/z=283 (M+); 1H NMR: 5.25 (s, 2 H) 7.44 (t, J=9.0 Hz, 2 H) 7.85-8.00 (m, 4 H) 8.19 (dd, J=9.8, 5.4 Hz, 2 H).

Workup

  1. customA 50 ml round-bottomed flask equipped with a magnetic stirrer and with a septum
  2. customthe precipitate formed
  3. filtrationis filtered off on a glass frit
  4. washwashed with 3 times 50 ml of isopropyl ether
  5. customThis, after drying under RP

Sources & evidence

ORD record
ord-ce722b075c8d4a94b973986594b54002
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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