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

HRID 2104400Notes

Reaction equation

HRID 2104400 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 solvent mixture of water (30 mL) and concentrated HCl (3.5 mL), and sodium nitrite (1.30 g) was added thereto under ice cooling, followed by stirring for 10 minutes. To the resultant mixture were added concentrated HCl (5.3 mL) and sodium tetrafluoroborate (6.90 g), followed by stirring for 30 minutes under ice cooling. The precipitate was collected by filtration, and was washed with water, methanol, and diethyl ether, to thereby give the title compound (2.63 g). The compound was directly used for the next reaction.

Workup

  1. additionwas added
  2. stirringby stirring for 30 minutes under ice cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwas washed with water, methanol, and diethyl ether

Sources & evidence

ORD record
ord-8256c73fbc384986919eedee05362cb5
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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