Diethyl Ether → 2-Bromo-4-chlorobenzenediazonium tetrafluoroborate

HRID 992484

Reaction equation

HRID 992484 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H+].[B-:11]([F:15])([F:14])([F:13])[F:12].[N:16]([O-])=O.[Na+].C(OCC)C>CCO>[F:12][B-:11]([F:15])([F:14])[F:13].[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[N+:4]#[N:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 28118Tetrafluoroboric acidHCID 701102-Bromo-4-chloroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 184127642-Bromo-4-chlorobenzenediazonium tetrafluoroborateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-4-chloroaniline (10.0 g, 48.4 mmol) and HBF4 in EtOH (60 mL) kept at 0° C. was treated with an aqueous solution (20 mL) of NaNO2 (3.34g, 48.4 mmol). After completion of the addition, diethyl ether (200 mL) was added to the mixture. The solid was collected by filtration, washed with water and dried under high vacuum affording the title compound (14.2 g, 96%) as white crystals.

Workup

  1. customkept at 0° C.
  2. additionwas added to the mixture
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-455616b784b7483eb55eb365e0f0b005
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Linked notes

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