Boron tribromide → HCID 68428755, compound

HRID 2240289Notes

Reaction equation

HRID 2240289 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[O:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)=[CH:9][CH:8]=1>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[O:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68428133HCID 68428133, compound

Product 1

HCID 68428755HCID 68428755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.5 g of boron tribromide are slowly added dropwise, at −60°, to a mixture of 70 ml of dichloromethane and 1.5 g of 1-methoxy-4-(5-oxo-2-tert-butyl-3,4-diaza-1-oxa-cyclopent-2-en-4-yl)-benzene. The reaction mixture is stirred at room temperature for 12 hours and then discharged onto ice/water. The aqueous mixture is extracted with dichloromethane, the extract is washed with water and concentrated and the residue is recrystallised from toluene/pentane, yielding 1-hydroxy-4-(5-oxo-2-tert-butyl-3,4-diaza-1-oxa-cyclopent-2-en-4-yl)-benzene, which melts at from 170° to 172°.

Workup

  1. extractionThe aqueous mixture is extracted with dichloromethane
  2. washthe extract is washed with water
  3. concentrationconcentrated
  4. customthe residue is recrystallised from toluene/pentane

Sources & evidence

ORD record
ord-51b37236371b45218905024b8fcdf736
Source dataset
uspto-grants-2010_05
Patent number
US07723362B2

Reaction notes

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