Hydrogen Bromide → 3-Bromo-2,6-dichlorobenzonitrile

HRID 1508176Notes

Reaction equation

HRID 1508176 reaction equation
OS(O)(=O)=O.N([O-])=O.[Na+].N[C:11]1[C:12]([Cl:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[C:14]#[N:15].[BrH:21]>C(O)(=O)C>[Br:21][C:11]1[C:12]([Cl:20])=[C:13]([C:16]([Cl:19])=[CH:17][CH:18]=1)[C:14]#[N:15]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 154052993-Amino-2,6-dichlorobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 712393713-Bromo-2,6-dichlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 1 mL of conc. H2SO4 was portionwise added sodium nitrite (1.38 mmol). After complete dissolution, a solution of 3-amino-2,6-dichlorobenzonitrile (1.24 mmol) in 2.5 mL glacial acetic acid was added at 0° C. After 30 min at 0° C., a precooled solution of CuBr (2.76 mmol) in 0.5 mL HBr (48% in H2O) was slowly added. The reaction was stirred at 0° C. for 45 min and then at RT for 45 min. The mixture was quenched with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give the desired product as brown solid.

Workup

  1. dissolutionAfter complete dissolution
  2. waitat RT for 45 min
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd4ee12fbcb24b63a764c221090ab5b3
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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