Cesium carbonate → {4-[5-(3-Bromophenyl) tetrazol-2-ylmethyl]benzyl}phosphonic acid dimethyl ester

HRID 349455

Reaction equation

HRID 349455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:13](=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][P:21]([CH:25](C)[C:26]1[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=1)(=[O:24])[O:22][CH3:23]>CN(C=O)C.C(OCC)(=O)C>[CH3:23][O:22][P:21]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:13][N:10]2[N:11]=[N:12][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)=[N:9]2)=[CH:30][CH:31]=1)(=[O:24])[O:20][CH3:19]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 40730565-(3-bromophenyl)-1H-1,2,3,4-tetrazoleHCID 86626606HCID 86626606, compound

Product 1

HCID 86626605{4-[5-(3-Bromophenyl) tetrazol-2-ylmethyl]benzyl}phosphonic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(3-bromophenyl)-2H-tetrazole (0.5 g, 2.22 mmol) in DMF (15 mL) was added cesium carbonate (0.94 g, 2.89) and the mixture stirred at room temperature for 15 minutes. To this was added (4-bromo-methylbenzyl) phosphonic acid dimethyl ester (0.85 g, 3.05 mmol) and the reaction mixture stirred over night at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over MgSO4, filtered, and the evaporated to dryness.

Workup

  1. stirringthe reaction mixture stirred over night at room temperature
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe evaporated to dryness

Sources & evidence

ORD record
ord-c479c7576f7a455e905f468b16856b1b
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Linked notes

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