Boron tribromide → HCID 22918451, compound

HRID 1376777Notes

Reaction equation

HRID 1376777 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)=[CH:22][C:21]=1[O:28]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[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])=[CH:22][C:21]=1[OH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22918358HCID 22918358, compound

Product 1

HCID 22918451HCID 22918451, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 100 mg (0.26 mmol) of 4-anilino-5-(2,4-dimethoxy-anilino)-phthalimide in 8 ml of chloroform, a solution of 120 μl (1.24 mmol) boron tribromide is added dropwise at RT. The reaction mixture is stirred for 5 hours at RT, is 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), the product fractions are combined and concentrated by evaporation. Recrystallization from ethyl acetate/dichloromethane/hexane yields the title compound in the form of yellow crystals, m.p. 155° C. (decomp.), FAB-MS: 362 [M+ +H].

Workup

  1. customis then quenched 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-a674519aaa3f4160aa6c3ccef9d36487
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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