4-(Bromomethyl)benzoic acid → 4-(Azidomethyl)benzoic acid

HRID 1680331Notes

Reaction equation

HRID 1680331 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CC(C)=O.O>[N:12]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[N+:13]=[N-:14]

Participants

5

Reactant 2

HCID 225994-(Bromomethyl)benzoic acidHCID 33557Sodium Azide

Product 1

HCID 205054704-(Azidomethyl)benzoic acidYield 90.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of p-bromomethylbenzoic acid (13.607 g, 63.3 mmol) in acetone (300 ml) and H2O (15ml) was added dropwise at room temperature a solution of NaN3 (4.123 g, 63.4mmol) in H2O (40 ml). The reaction mixture was stirred at room temperature overnight (ca 20 h). After evaporation of the acetone, the residual solid was suspended in water and filtered, yielding 10.13 g (57.2 mmol, 90.3%) of p-azidomethylbenzoic acid as a white powder: 1Hmr (DMSO-d6 δ: 4.57 (2H, s, --CH3N3), 7.43-7.55-7.93-8.07 (4H, A2'B2', aromatic Hs) and 12.7 ppm (br, s, --CO2H): ir (nujol) νmax : (--N3) and 1670 cm-1 (--CO2H).

Workup

  1. customAfter evaporation of the acetone
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a8bd29a1b2fd4978bf6b8cf734ff5302
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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