Boron tribromide → HCID 22918451, compound

HRID 2396062Notes

Reaction equation

HRID 2396062 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 concentratedby evaporation. Excluding light, the evaporation residue is chromatographedwith 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 and concentratedby evaporation
  6. temperatureis cooled with ice-water (double jacket)
  7. concentrationconcentrated by evaporation
  8. customRecrystallization from ethyl acetate/dichloromethane/hexane

Sources & evidence

ORD record
ord-8ed3788a4fd14f7c8b2a27fe4c83afcf
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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