Boron tribromide → HCID 22918394, compound

HRID 1376781Notes

Reaction equation

HRID 1376781 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[NH:14][C:12](=[O:13])[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([O:28]C)[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[O:16])[NH:14][C:12](=[O:13])[C:11]2=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:28])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22918430HCID 22918430, compound

Product 1

HCID 22918394HCID 22918394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 219 mg (0.56 mmol) of 4-anilino-5-(3,4-dimethoxy-anilino)-phthalimide in 5 ml of dichloromethane, a solution of 270 μl (2.8 mmol) boron tribromide in 3 ml of dichloromethane is added dropwise at RT. The reaction mixture is stirred for 5 hours at RT and then quenched with 5 ml of water, and the phases are separated. The water phase is extracted three times with ethyl acetate. The organic phases are combined and washed twice with water, dried over magnesium sulfate and concentrated by evaporation. Excluding light, the evaporation residue is chromatographed with ethylacetate/hexane 2:1 on a silica gel column (precoated with 0.1 g of sodium ascorbate per g silica gel) that is cooled with ice-water (double jacket), and the product fractions are combined and concentrated by evaporation. Recrystallization from ethyl acetate/dichloromethane/hexane yields the title compound in the form of orange crystals, FAB-MS: 362 [M+ +H].

Workup

  1. customquenched with 5 ml of water
  2. customthe phases are separated
  3. extractionThe water phase is extracted three times with ethyl acetate
  4. washwashed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customthe evaporation residue is chromatographed with ethylacetate/hexane 2:1 on a silica gel column (precoated with 0.1 g of sodium ascorbate per g silica gel) that
  8. temperatureis cooled with ice-water (double jacket)
  9. concentrationconcentrated by evaporation
  10. customRecrystallization from ethyl acetate/dichloromethane/hexane

Sources & evidence

ORD record
ord-dbb196b9f49849828d9623274f863dd0
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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