Hydrochloric Acid → HCID 86605681, compound

HRID 860965Notes

Reaction equation

HRID 860965 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH3:25])=[C:5]([CH:9]=[C:10]([Cl:24])[C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[C:15]([Br:23])[CH:14]=1)[C:6]([OH:8])=[O:7].[CH3:26]O>>[Cl:2][C:3]1[C:4]([CH3:25])=[C:5]([CH:9]=[C:10]([Cl:24])[C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[C:15]([Br:23])[CH:14]=1)[C:6]([O:8][CH3:26])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86605682HCID 86605682, compound

Product 1

HCID 86605681HCID 86605681, compound

Conditions

Temperature
20 °C

Procedure

HCl gas was bubbled through a solution of 3,5-dichloro-2-methyl-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoic acid (375 mg, 0.86 mmol) in MeOH (20 mL) for 5 min. Upon stirring at 20° C. for 22 hr, HPLC analysis revealed esterification was complete. After removal of the solvent under vacuum and dissolution of the residue in EtOAc, the EtOAc layer was washed 2× with H2O then with brine prior to drying over MgSO4. Removal of the volatiles yielded 391 mg of crude methyl 3,5-dichloro-2-methyl-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoate as a brown solid which was not further purified.

Workup

  1. customAfter removal of the solvent
  2. dissolutionunder vacuum and dissolution of the residue in EtOAc
  3. washthe EtOAc layer was washed 2× with H2O
  4. dry with materialwith brine prior to drying over MgSO4
  5. customRemoval of the volatiles

Sources & evidence

ORD record
ord-685c256875e740e4bcfbaf57d55f7276
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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