Hydrochloric Acid → 5-Carboxy-3-nitro-2phenylbenzenediazonium tetrafluoroborate

HRID 1605546Notes

Reaction equation

HRID 1605546 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[N:20]([O-])=O.[K+].Cl.[B:25]([F:28])([F:27])[F:26].[FH:29]>[OH-].[K+].C(O)(=O)C>[F:26][B-:25]([F:29])([F:28])[F:27].[C:5]([C:4]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]([N+:1]#[N:20])[CH:3]=1)([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516910Potassium nitriteHCID 9855450Trifluoroborane HydrofluorideHCID 124087693-Amino-5-nitro-4-phenylbenzoic acid

Product 1

HCID 215468605-Carboxy-3-nitro-2phenylbenzenediazonium tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14797Potassium HydroxideSolvent

Procedure

A hot solution of 3-amino-5-nitro-4-phenylbenzoic acid (39 g; prepared as in Example 1, step C) and potassium nitrite (15 g) in 1 N potassium hydroxide (260 ml) is added dropwise to a mixture of acetic acid (150 ml) and conc. hydrochloric acid (150 ml), while stirring vigorously at -2° to 2° C. After additional stirring at this temperature for about 10 minutes, 50% hydrofluoroboric acid (100 ml) is added during about 5 minutes, keeping the temperature below 5° C by external cooling. After additional stirring at about -10° C for 1 hour, the precipitated 5-carboxy-3-nitro-2-phenylbenzenediazonium tetrafluoroborate is collected by filtration, washed with icecold water (two portions of each 25 ml) and dried.

Workup

  1. stirringAfter additional stirring at this temperature for about 10 minutes
  2. customthe temperature below 5° C
  3. stirringAfter additional stirring at about -10° C for 1 hour
  4. filtrationthe precipitated 5-carboxy-3-nitro-2-phenylbenzenediazonium tetrafluoroborate is collected by filtration
  5. washwashed with icecold water (two portions of each 25 ml) and
  6. customdried

Sources & evidence

ORD record
ord-155e57820687425d8335511f5d034cc6
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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