Cesium carbonate → 2-Chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1750482Notes

Reaction equation

HRID 1750482 reaction equation
[N:1]1[NH:2][N:3]=[CH:4][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.Br[C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25]([OH:27])=[O:26]>CN(C=O)C.[Cu]I>[Cl:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:23]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)[C:24]=1[C:25]([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 331252-bromo-6-chlorobenzoic acidHCID 675161H-1,2,3-TriazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 846887842-Chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To the solution of 2H-1,2,3-triazole (CAS number 288-36-8; 4.0 g, 57.97 mmol) in DMF (14 ml) was added cesium carbonate (18.84 g, 57.97 mmol), trans-1-N,2-N-dimethylcyclohexane-1,2-diamine (0.510 g, 5.80 mmol), copper(I) iodide (0.276 g, 1.45 mmol) and 2-bromo-6-chlorobenzoic acid (CAS number 93224-85-2; 6.78 g, 28.98 mmol) at 0-10° C. The reaction was subjected to microwave irradiation at 125° C. for 15 minutes and was then partitioned between ethyl acetate (3×100 ml) and water (100 ml). The aqueous layer was acidified with 2M HCl (aq) to give pH 2 and then extracted with ethyl acetate (3×100 ml). The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was then purified by column chromatography (0-3% methanol/DCM) to afford the title compound.

Workup

  1. customirradiation at 125° C. for 15 minutes
  2. customwas then partitioned between ethyl acetate (3×100 ml) and water (100 ml)
  3. customto give pH 2
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThis was then purified by column chromatography (0-3% methanol/DCM)

Sources & evidence

ORD record
ord-ad1e9b4152ff40f2a0b070400288014a
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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