Sodium Azide → 2-Chloro-3-fluoroaniline

HRID 1840379Notes

Reaction equation

HRID 1840379 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.[N-:12]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[NH2:12]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 3026202-Chloro-3-fluorobenzoic acid

Product 1

HCID 888842-Chloro-3-fluoroanilineYield 1,024.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-3-fluorobenzoic acid (4 g, 23 mmol) in CHCl3 (50 mL), sulfonic acid (64 mL) was added and then sodium azide (2.62 g, 1.75 mmol) was added by portion. After addition, the reaction mixture was stirred at 50° C. for 16 hours. The solvent was evaporated and basicified with ammonium hydroxide at ice-bath. Then was extracted with ethyl acetate (3×). The combine organic phase was dried and conc. to give the desired product (2.61 g, 78%). LC-MS m/z 146.2 (M+).

Workup

  1. additionAfter addition
  2. customThe solvent was evaporated
  3. custombasicified with ammonium hydroxide at ice-bath
  4. extractionThen was extracted with ethyl acetate (3×)
  5. customThe combine organic phase was dried

Sources & evidence

ORD record
ord-dac016e661984a82b965e223942b0675
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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