M-Xylene → HCID 18956464, compound

HRID 2380007Notes

Reaction equation

HRID 2380007 reaction equation
Br[C:2]([F:33])([F:32])[C:3](F)([F:30])[O:4][C:5]1[CH:29]=[CH:28][CH:27]=[C:7]2[C:8]([N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20](F)([F:25])[C:21]([F:24])([F:23])Br)=[CH:15][CH:14]=3)[C:11](=[O:12])[C:6]=12)=[O:9].BrC(F)(F)C(F)(F)OC1C=CC(N)=CC=1.BrC(F)(F)C(F)(F)OC1C=CC=C2C(OC(=O)C=12)=O.C1(C)C=CC=C(C)C=1>CN1CCCC1=O>[F:30][C:3]([O:4][C:5]1[CH:29]=[CH:28][CH:27]=[C:7]2[C:8]([N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:25])=[C:21]([F:23])[F:24])=[CH:17][CH:18]=3)[C:11](=[O:12])[C:6]=12)=[O:9])=[C:2]([F:33])[F:32]

Participants

6

Reactant 4

HCID 7929M-XyleneHCID 18956456HCID 18956456, compoundHCID 18956462HCID 18956462, compound2×HCID 53640275HCID 53640275, compound

Product 1

HCID 18956464HCID 18956464, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

3-(2-Bromotetrafluoroethoxy)-N-(4-(2-bromotetrafluoroethoxy)phenyl)phthalimide Into a 250 ml round bottomed flask fitted with a mechanical stirrer and a Dean-Stark trap is placed 4-(2-bromotetrafluoroethoxy)aniline (3.4 g, 0.0118 mole) in 40 ml of N-methylpyrrolidinone (NMP). In a separate flask, 3-(2-bromotetrafluoroethoxy)phthalic anhydride (3.0 g, 0.00874 mole) is dissolved in 20 ml of NMP and is added slowly drop wise over 15 minutes to the stirring solution of 4-(2-bromotetrafluoroethoxy)aniline in NMP. The mixture is stirred for 30 minutes at room temperature, after which m-xylene (6 ml) is added and the suspension is heated to 40° C. After heating at 40° C. for 1 hour the is heated to reflux (181° C.) and is refluxed for 6.5 hours to remove water azeotropically. Upon cooling the solvent is removed by evaporation under vacuum and the solid precipitate is recrystallized from dichloromethane/hexane solution (2:1) to provide the product as a light yellow crystalline solid (4.37 g, 81.5 percent yield) with a melting point of 172°-172.5° C.

Workup

  1. temperaturethe suspension is heated to 40° C
  2. temperatureAfter heating at 40° C. for 1 hour the
  3. temperatureis heated
  4. temperatureto reflux (181° C.)
  5. temperatureis refluxed for 6.5 hours
  6. customto remove water azeotropically
  7. temperatureUpon cooling the solvent
  8. customis removed by evaporation under vacuum
  9. customthe solid precipitate is recrystallized from dichloromethane/hexane solution (2:1)

Sources & evidence

ORD record
ord-549f028c97de4aecabc90d4b66b73a74
Source dataset
uspto-grants-1994_11
Patent number
US05364917

Reaction notes

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