3-Chloroaniline → Benzenediazonium, 3-chloro-, tetrafluoroborate(1-) (1:1)

HRID 902873Notes

Reaction equation

HRID 902873 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[N:9]([O-])=O.[Na+].[F:13][B-:14]([F:17])([F:16])[F:15].[Na+]>O.Cl>[F:13][B-:14]([F:17])([F:16])[F:15].[Cl:1][C:2]1[CH:3]=[C:4]([N+:5]#[N:9])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 79323-ChloroanilineHCID 4343483Sodium TetrafluoroborateHCID 23668193Sodium Nitrite

Product 1

HCID 164600Benzenediazonium, 3-chloro-, tetrafluoroborate(1-) (1:1)Yield 74.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

3-Chloroaniline (2.0 g) was dissolved in a mixed solvent of water (30 ml) and concentrated hydrochloric acid (3.5 ml), and sodium nitrite (1.30 g) was added under ice cooling to stir the mixture for 10 minutes. After concentrated hydrochloric acid (5.3 ml) and sodium tetrafluoroborate (6.90 g) were added to the reaction mixture to stir the mixture for 30 minutes under ice cooling, precipitate was collected by filtration and washed with water, methanol and diethyl ether to obtain the title compound (2.63 g). This compound was used in the next reaction as it was.

Workup

  1. additionwas added under ice cooling
  2. stirringto stir the mixture for 30 minutes under ice cooling
  3. filtrationprecipitate was collected by filtration
  4. washwashed with water, methanol and diethyl ether

Sources & evidence

ORD record
ord-396befa0a417499ea60b760bbf498bb7
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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