Hydrogen Bromide → 6-Bromonaphthalene-2-sulfonic acid

HRID 1595460Notes

Reaction equation

HRID 1595460 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16]([OH:19])(=[O:18])=[O:17])[CH:10]=[CH:9]2.Cl.[BrH:21]>O>[Br:21][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16]([OH:19])(=[O:18])=[O:17])[CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 71166-Amino-2-naphthalenesulfonic acidHCID 23668193Sodium Nitrite

Product 1

HCID 129891986-Bromonaphthalene-2-sulfonic acidYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (2.7 g) in water (5 ml) was added during 2 hours to a stirred mixture of 6-amino-2-naphthalene-sulphonic acid (8.8 g), dilute aqueous hydrochloric acid (2.8% weight/volume, 20 ml) and water (15 ml) which had been cooled to 0° C. The mixture was stirred at 0° C. for 30 minutes and poured onto a stirred suspension of cuprous bromide (5.34 g) in dilute aqueous hydrobromic acid (2.8%, 20 ml). The mixture was stored at ambient temperature for 18 hours. The mixture was evaporated to give 6-bromo-2-naphthalenesulphonic acid which was used without further purification.

Workup

  1. waitThe mixture was stored at ambient temperature for 18 hours
  2. customThe mixture was evaporated

Sources & evidence

ORD record
ord-fe8bfbd5315c4d1f8c254ec83f907c82
Source dataset
uspto-grants-2001_09
Patent number
US06288103B1

Reaction notes

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