Boron tribromide → HCID 22918414, compound

HRID 1376783Notes

Reaction equation

HRID 1376783 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]=[C:24]([O:26]C)[C:23]([O:28]C)=[C:22]([O:30]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]=[C:24]([OH:26])[C:23]([OH:28])=[C:22]([OH:30])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22918385HCID 22918385, compound

Product 1

HCID 22918414HCID 22918414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 78 mg (0.18 mmol) of 4-anilino-5-(3,4,5-trimethoxy-anilino)phthalimide (Example 27) in 4 ml of dichloromethane, a solution of 314 μl (3.24 mmol) boron tribromide is added dropwise at RT. The reaction mixture is stirred for 4 hours at RT, is then cooled to 0° and 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/dichloromethane 4:1 on a silica gel column (precoated with 0.4 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 yielding the title compound in the form of dark red crystals, m.p. 152° C. (decomp.), FAB-MS: 378 [M+ +H].

Workup

  1. temperatureis then cooled to 0°
  2. customquenched with 5 ml of water
  3. customthe phases are separated
  4. extractionThe water phase is extracted three times with ethyl acetate
  5. washwashed twice with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customthe evaporation residue is chromatographed with ethylacetate/dichloromethane 4:1 on a silica gel column (precoated with 0.4 g of sodium ascorbate per g silica gel) that
  9. temperatureis cooled with ice-water (double jacket)
  10. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1cae5a3d95824d02900d8c7e4d440337
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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