3-Bromo-4-methylbenzoic acid → 3-Bromo-5-iodo-4-methylbenzoic acid

HRID 337628Notes

Reaction equation

HRID 337628 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[I:12]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 821303-Bromo-4-methylbenzoic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 581708803-Bromo-5-iodo-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 3-bromo-4-methylbenzoic acid in 96% sulphuric acid (˜0.58 M reaction concentration) was added N-iodosuccinimide (1.1 equiv.) over 1 h maintaining the temperature between 10 and 30° C. The reaction mixture was aged for 10 min then quenched into water. The slurry was filtered and washed with water, sodium bisulfite solution and then finally with water to give the title compound as an off-white solid. 1H NMR (400 MHz, dmso-d6): δ 13.4 (br s, 1 H); 8.30 (s, 1 H); 8.00 (s, 1 H); 2.64 (s, 3 H). HRMS (ES, M−H) Calcd 338.8518. Found 338.8516.

Workup

  1. temperaturemaintaining the temperature between 10 and 30° C
  2. customthen quenched into water
  3. filtrationThe slurry was filtered
  4. washwashed with water, sodium bisulfite solution

Sources & evidence

ORD record
ord-f642eb82eb844aef963e648f9931f949
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…