Sulfuric Acid → HCID 59287856, compound

HRID 1803465Notes

Reaction equation

HRID 1803465 reaction equation
[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[CH3:20])=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=O.S(=O)(=O)(O)O>CCOC(C)=O.CO>[Br:1][C:2]1[C:3]2[O:12][C:13]3[C:18](=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=3[CH3:20])[C:5](=[O:7])[C:4]=2[CH:8]=[C:9]([CH3:11])[CH:10]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59287852HCID 59287852, compound

Product 1

HCID 59287856HCID 59287856, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Following the method in Example 1, the crude 3-bromo-2-(2,3-dimethylphenoxy)-5-methyl-benzoic acid (16) was treated with sulfuric acid and recrystallized from EtOAc/MeOH to yield a light yellow solid, and the yield was 91%: Mp (EtOAc/MeOH) 236-238° C.; 1H-NMR [(CD3)2SO] δ 8.12 (s, 1H), 8.10 (d, J=7.9 Hz, 1H), 7.75 (d, J=7.9 Hz, 1H), 7.42 (s, 1H), 2.55 (s, 3H), 2.46 (s, 3H); 13C-NMR δ 171.6, 153.6, 152.1, 143.3, 136.9, 128.0, 125.6, 125.3, 124.5, 123.9, 120.2, 120.0, 119.7, 21.8, 20.3, 12.4.

Workup

  1. customrecrystallized from EtOAc/MeOH
  2. customto yield a light yellow solid

Sources & evidence

ORD record
ord-211e1ebc3f3b48c48f1c59491ade0ed7
Source dataset
uspto-grants-2013_01
Patent number
US08350065B2

Reaction notes

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