Hydrochloric Acid → 2-Azido-4-bromobenzoic acid

HRID 270680

Reaction equation

HRID 270680 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.N([O-])=O.[Na+].[N-:17]=[N+:18]=[N-].[Na+].CC([O-])=O.[Na+]>O>[N:1]([C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[N+:17]=[N-:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 886912-Amino-4-bromobenzoic acidHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 860515482-Azido-4-bromobenzoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 2-amino-4-bromobenzoic acid (8.4 g, 0.039 mol) in a mixture of concentrated HCl (70 mL) and H2O (100 mL) was added a solution of NaNO2 (2.8 g, 0.044 mol) in H2O (40 mL) such that the reaction temperature did not rise above 5° C. After addition was complete the resulting slurry was stirred for 15 min and the cold mixture added in aliquots to a solution of NaN3 (2.5 g, 0.039 mol) and NaOAc (38 g, 0.47 mol) in H2O (80 mL) at room temperature. The resulting slurry was stirred for 30 min and the solid collected by filtration giving 6.4 g (68% yield) of product as a tan powder. 1H NMR (360 MHz, DMSO): 7.46 (1H, dd, J 1.4 and 7.5 Hz), 7.57 (1H, d, J 1.4 Hz), 7.70 (1H, d, J 7.5 Hz).

Workup

  1. customdid not rise above 5° C
  2. additionAfter addition
  3. stirringThe resulting slurry was stirred for 30 min
  4. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-70be7ff4632b4714a00d4f6df4eb851d
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Linked notes

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