Benzyl Bromide → 2-(1-benzyl-1H-tetrazol-5-yl)benzaldehyde

HRID 1040406Notes

Reaction equation

HRID 1040406 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4][N:3]=[N:2]1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C.CCCCCC.CN(C)C=O>[CH2:25]([N:4]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:1][N:2]=[N:3]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 178519511HCID 178519511, compound

Product 1

HCID 867621002-(1-benzyl-1H-tetrazol-5-yl)benzaldehydeYield 83.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1H-tetrazol-5-yl)benzaldehyde (100 mg, 0.57 mmol, synthesized in Example 117 (1)) in a 3:1 solution (4 mL) of tetrahydrofuran and N,N-dimethylformamide was added potassium carbonate (0.12 g, 0.86 mmol), benzyl bromide (82 μL, 0.69 mmol) at room temperature, successively. After being stirred at room temperature overnight, the reaction mixture was diluted with a 5:2 solution (7 mL) of ethyl acetate and hexane. The solution was washed with water twice, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 80/20) to obtain the title compound (126 mg, 83%).

Workup

  1. customat room temperature
  2. washThe solution was washed with water twice
  3. dry with materialbrine, and dried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 80/20)

Sources & evidence

ORD record
ord-f19a8fd833f4449dbed02561f810f99b
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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