Benzyl Bromide → Ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoate

HRID 598335Notes

Reaction equation

HRID 598335 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[CH:10][C:11]([N:19]2[C:23]([CH3:24])=[N:22][N:21]=[N:20]2)=[C:12]([CH:18]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([O:7][C:8]1[CH:9]=[CH:10][C:11]([N:19]2[C:23]([CH3:24])=[N:22][N:21]=[N:20]2)=[C:12]([CH:18]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67050952Ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoate

Product 1

HCID 67051161Ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoateYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (110 g, 0.793 mol) was added to a solution of ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoate (98.5 g, 0.397 mol) in 500 mL of DMF. After vigorous stirring for 30 minutes, benzyl bromide (75 g, 0.438) was added and the reaction was stirred overnight. The solution was filtered and then concentrated under reduced pressure (at 50° C.). The resulting solid was slurried in 400 mL of dichloromethane and filtered. The filtrate was concentrated under reduced pressure to give 115 g of ethyl 5-benzyloxy-2-(5-methyltetrazol-1-yl)benzoate as a brown oil.

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationThe solution was filtered
  3. concentrationconcentrated under reduced pressure (at 50° C.)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d9ff29bed904a1fbf3749e3c7593878
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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