Benzyl Bromide → Benzyl 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]butyrate

HRID 257730Notes

Reaction equation

HRID 257730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:12][CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(C(C)=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)([CH2:12][CH3:13])[C:9]([O:11][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19956952HCID 19956952, compound

Product 1

HCID 20085196Benzyl 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]butyrateYield 77%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a 300 mL flask stirring under nitrogen was charged 4.19 g (0.015 mole) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]-butanoic acid in 75 mL of methyl ethyl ketone. To the slurry was added 2.83 g (0.0157 mole) of potassium carbonate and the mixture was heated to reflux. After 30 minutes, 2.56 g (0.01575 mole) of benzyl bromide was added and the mixture was stirred at reflux for 2 hours then at 50° C. for 12 hours. After monitoring by GLC showed the consumption of starting material, the reaction was quenched by adding 20 mL of saturated sodium bicarbonate and 100 mL of ether. The phases were separated and the ether phase was washed with saturated sodium bicarbonate (2×50 mL) then with 50 mL of brine, dried and concentrated, giving 4.26 g (77% yield) of a thick oil, Example 177 of Table 1.

Workup

  1. temperaturethe mixture was heated to reflux
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 2 hours
  4. waitat 50° C. for 12 hours
  5. customthe consumption of starting material
  6. customthe reaction was quenched
  7. additionby adding 20 mL of saturated sodium bicarbonate and 100 mL of ether
  8. customThe phases were separated
  9. washthe ether phase was washed with saturated sodium bicarbonate (2×50 mL)
  10. dry with materialwith 50 mL of brine, dried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e164cc1cbdee46639e038e0722d18ea8
Source dataset
uspto-grants-1993_11
Patent number
US05264415

Reaction notes

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