Sodium Azide → 4-Azidomethyl-2-phenylbenzoic acid methyl ester

HRID 2121243Notes

Reaction equation

HRID 2121243 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:19]=[N+:20]=[N-:21])=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 18474540Methyl 4-bromomethyl-2-phenylbenzoate

Product 1

HCID 544461164-Azidomethyl-2-phenylbenzoic acid methyl esterYield 77.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-bromomethyl-2-phenylbenzoic acid methyl ester (1.5 g, 4.9 mmol), sodium azide (1.28 g, 19.7 mmol) and tetrabutylammonium iodide (1.3 g, 4.9 mmol) in DMF (16 mL) was heated at 75° C. for 18 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (15% ethyl acetate-hexanes) to give the desired azide as a colorless oil (1.01 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4feef79cc3d44d65a86448b95c59bf3a
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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