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

HRID 2383164Notes

Reaction equation

HRID 2383164 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-d75276f485cc4c5dbff92285f9f60f9d
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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