Boron tribromide → HCID 86587319, compound

HRID 352262Notes

Reaction equation

HRID 352262 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9]C)[C:5]([F:11])=[C:4]([F:12])[C:3]=1[C:13]1[C:14]([NH:16][C:17](=[O:19])[CH:18]=1)=[O:15].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[C:13]1[C:14]([NH:16][C:17](=[O:19])[CH:18]=1)=[O:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86587320HCID 86587320, compound

Product 1

HCID 86587319HCID 86587319, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2 g of the 2,3,5,6-tetrafluoro-4-methoxyphenylmaleimide obtained in Example 1 was dissolved in 10 ml of dry methylene chloride. Thereto was added 15 ml of a methylene chloride solution containing 1 M of boron tribromide. The mixture was stirred at room temperature for 3 days in an argon atmosphere. The reaction mixture was poured into 200 ml of ice water. The organic layer was extracted with ether. The ether layer was washed with an aqueous sodium chloride solution and dried over magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove ether. The residue was recrystallized from ligroin/toluene to obtain 1 g of an intended compound (yield: 53%).

Workup

  1. extractionThe organic layer was extracted with ether
  2. washThe ether layer was washed with an aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe resulting solution was subjected to vacuum distillation
  5. customto remove ether
  6. customThe residue was recrystallized from ligroin/toluene

Sources & evidence

ORD record
ord-3cc35e149925422db194a31df56dbcff
Source dataset
uspto-grants-2004_06
Patent number
US06746722B2

Reaction notes

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