Ethyl 3-bromobenzoate → Ethyl 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoate

HRID 1820251Notes

Reaction equation

HRID 1820251 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1)[CH3:2].[CH2:13]([O:20][CH2:21][N:22]1[N:26]=[N:25][C:24]([Sn](CCCC)(CCCC)CCCC)=[N:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([O:20][CH2:21][N:22]1[N:26]=[N:25][C:24]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:12])=[N:23]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 90488Ethyl 3-bromobenzoateHCID 113405612-((Phenylmethoxy)methyl)-5-(tributylstannyl)-2H-tetrazole

Product 1

HCID 57888757Ethyl 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of ethyl-3-bromobenzoate (0.47 g, 2.05 mmol) and 2-(benzyloxymethyl)-5-(tributylstannyl)-2H-tetrazole in toluene (20 mL) was degassed under vacuum and argon. To this solution was added copper (I) iodide (20 mg, 0.20 mmol) and tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.10 mmol), and the mixture was again degassed under vacuum and argon. The flask and condenser were covered in foil to exclude light, and the reaction was heated at reflux temperature for 3 hours. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated in-vacuo. The residue was purified over a 3.5×12 cm silica gel column, eluting with 5% then 10% then 15% ethyl acetate/hexanes to yield the title compound as a colorless oil which contained 5% of a tributyltin impurity. MS (ESI+)=339.22, (M+H)+. The oil was used as-is in the next step.

Workup

  1. customthe mixture was again degassed under vacuum and argon
  2. temperaturethe reaction was heated
  3. temperatureat reflux temperature for 3 hours
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated in-vacuo
  6. customThe residue was purified over a 3.5×12 cm silica gel column
  7. washeluting with 5%

Sources & evidence

ORD record
ord-6feeb0927652433d93bdbd7b94b6b7e1
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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