Tetrafluoroboric acid → 5-Bromo-2-methylbenzenediazonium tetrafluoroborate

HRID 2240513Notes

Reaction equation

HRID 2240513 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][C:6]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:7]=1[NH2:8].[F:14][B-:15]([F:18])([F:17])[F:16].[H+]>O>[F:14][B-:15]([F:18])([F:17])[F:16].[Br:13][C:10]1[CH:11]=[CH:12][C:6]([CH3:5])=[C:7]([N+:8]#[N:1])[CH:9]=1

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 27348055-Bromo-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 805030315-Bromo-2-methylbenzenediazonium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium nitrite (0.56 g) in water(2.0 mL) was slowly added to a mixture of 2-methyl-5-bromoaniline (1.50g) in tetrafluoroboric acid (6.0 mL) and water (4.0 mL) at 0-5° C. After addition, the reaction was stirred at room temperature for 30 min. The mixture was cooled to 0° C., filtered, washed with cold water, cold methanol and ether. The mixture was then dried to provide the product 5-bromo-2-methylphenyldiazonium tetrafluroborate (1.90 g).

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled to 0° C.
  3. filtrationfiltered
  4. washwashed with cold water, cold methanol and ether
  5. customThe mixture was then dried

Sources & evidence

ORD record
ord-8188338000224d38b330ef3a1f5c6d42
Source dataset
uspto-grants-2010_05
Patent number
US07723349B2

Reaction notes

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