Boron tribromide → HCID 15069382, compound

HRID 1736816Notes

Reaction equation

HRID 1736816 reaction equation
B(Br)(Br)Br.[CH:5]1([CH2:11][C:12]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]([OH:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)[C:15]3[CH:33]=[C:34]([O:39]C)[C:35]([O:37]C)=[CH:36][C:14]=3[N:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>ClCCl>[CH:5]1([CH2:11][C:12]2[N:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[C:25]([C:30]([OH:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][CH:23]=3)[C:15]3[CH:33]=[C:34]([OH:39])[C:35]([OH:37])=[CH:36][C:14]=3[N:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15069357HCID 15069357, compound

Product 1

HCID 15069382HCID 15069382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.29 ml (3 mmol) of boron tribromide is added dropwise to a suspension of 242 mg (0.5 mmol) of 4'-[(2-cyclohexylmethyl-5,6-dimethoxy-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid in 25 ml of dichloromethane at -5° C. When the addition is complete, the cooling bath is removed and the mixture is stirred at ambient temperature for 5 hours. 20 ml of methanol are then added while the mixture is cooled with ice, then the reaction mixture is evaporated to dryness and the residue is suspended in 10 ml of water while stirring. The crude product precipitated is filtered off under suction, washed with a further 10 ml of water, dried and chromatographed over a silica gel column (eluting agent: dichloromethane/ethanol=9:1).

Workup

  1. additionWhen the addition
  2. customthe cooling bath is removed
  3. addition20 ml of methanol are then added while the mixture
  4. temperatureis cooled with ice
  5. customthe reaction mixture is evaporated to dryness
  6. stirringwhile stirring
  7. customThe crude product precipitated
  8. filtrationis filtered off under suction
  9. washwashed with a further 10 ml of water
  10. customdried
  11. customchromatographed over a silica gel column (eluting agent: dichloromethane/ethanol=9:1)

Sources & evidence

ORD record
ord-a3527c13998743738f0d74e2b99520ba
Source dataset
uspto-grants-1996_07
Patent number
US05541229

Reaction notes

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