Benzyl Bromide → HCID 178515913, compound

HRID 1839914Notes

Reaction equation

HRID 1839914 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([N:3]1[N:4]=[C:5]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[NH:1][NH:2]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8636344-(2-Trityl-2H-tetrazol-5-ylmethyl)-phenol

Product 1

HCID 178515913HCID 178515913, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A 20 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, a rubber septum and a reflux condenser was charged with acetone (25 mL), 4-(2H-tetrazol-5-yl)phenol (50 mg, 0.31 mmol) and K2CO3 (213 mg, 1.54 mmol). The reaction mixture was treated with benzylbromide (37 μL, 0.31 mmol) and heated at 50° C. for 18 h. The reaction mixture was cooled to ambient temperature and filtered to remove the K2CO3 and the filtrate was concentrated to dryness. The resulting residue was triturated with 3 M aqueous NaOH and extracted with ethyl acetate. The aqueous phase was separated and treated with HCl (conc.). The precipitate was collected and subjected to flash chromatography (SiO2, 30% ethyl acetate/hexane) to afford the title product as a white solid (57 mg, 74%). This procedure was repeated on a 3 g scale in 50% yield.

Workup

  1. customA 20 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationfiltered
  4. customto remove the K2CO3
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe resulting residue was triturated with 3 M aqueous NaOH
  7. extractionextracted with ethyl acetate
  8. customThe aqueous phase was separated
  9. additiontreated with HCl (conc.)
  10. customThe precipitate was collected

Sources & evidence

ORD record
ord-ad4642fa625c4fc3a477b70f0e59628d
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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