Sodium Azide → 4-Azidomethyl-2-(2-methylphenyl)benzoic acid methyl ester

HRID 383160Notes

Reaction equation

HRID 383160 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]>CN(C=O)C.CCOC(C)=O>[CH3:5][O:6][C:7](=[O:23])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:1]=[N+:2]=[N-:3])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 234362594-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester

Product 1

HCID 206998904-Azidomethyl-2-(2-methylphenyl)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture at 0° C. under N2 of sodium azide (1.47 g, 22.6 mmol) in anhydrous DMF (30 mL) was added a solution of 4-bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester (6.00 g, 18.8 mmol), prepared as in Example 1178A-D, in anhydrous DMF (10 mL). Reaction stirred overnight at room temperature. Reaction diluted with EtOAc and washed with water and brine. Organic layer dried with Na2SO4, filtered, and concentrated in vacuo.

Workup

  1. customReaction
  2. customReaction
  3. washwashed with water and brine
  4. dry with materialOrganic layer dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-461d450d66a7499eb0d30f0b3c899cc5
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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