Hydrogen Bromide → 5-Bromoisophthalic acid

HRID 1925197Notes

Reaction equation

HRID 1925197 reaction equation
N[C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[BrH:14].N([O-])=O.[Na+]>O>[Br:14][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 668335-Aminoisophthalic acidHCID 23668193Sodium Nitrite

Product 1

HCID 900735-Bromoisophthalic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

99.18 g (0.55 mol) of 5-aminoisophthalic acid, 165 mL of 48 weight % hydrobromic acid and 150 mL of distilled water were charged in a 1 L four-neck flask equipped with a thermometer, an agitator and a dropping funnel, and then agitated. The flask was cooled to 5° C. or below, and 525 mL of distilled water containing 39.4 g (0.57 mol) of sodium nitrite was added dropwise for an hour, thus obtaining diazonium aqueous solution. 94.25 g (0.66 mol) of cuprous bromide and 45 mL of 48 weight % hydrobromic acid were charged in a 3 L four-neck flask equipped with a thermometer, a Dimroth condenser, a dropping funnel and an agitator, and agitated.

Workup

  1. customequipped with a thermometer
  2. temperatureThe flask was cooled to 5° C. or below
  3. customequipped with a thermometer
  4. stirringa Dimroth condenser, a dropping funnel and an agitator, and agitated

Sources & evidence

ORD record
ord-ed1719f38e2041e79ca34d0006a1214f
Source dataset
uspto-grants-2012_05
Patent number
US08178631B2

Reaction notes

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