Boron tribromide → HCID 15055906, compound

HRID 330025Notes

Reaction equation

HRID 330025 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([S:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([S:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1)[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 14098085HCID 14098085, compound

Product 1

HCID 15055906HCID 15055906, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

814 μl of a 1M aqueous solution of boron tribromide in methylene chloride were added to a solution of 300 mg of methyl 4-[1-(2-methoxyphenyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 9) in 1.2 ml of methylene chloride at -78° C., and the resulting mixture was allowed to react at room temperature for 5 hours, and then poured into ice-water and stirred for 30 minutes. At the end of this time, the reaction mixture was neutralized with an aqueous solution of sodium bicarbonate, and then extracted with chloroform. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography eluted with a 30:1 by volume mixture of chloroform and methanol, to give 25 mg of the title compound as an oil.

Workup

  1. customto react at room temperature for 5 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation
  6. customthe residue was purified by silica gel column chromatography
  7. washeluted with a 30:1 by volume mixture of chloroform and methanol

Sources & evidence

ORD record
ord-df5be7c2e976481eb1a1e204b0693440
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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