3,5-Dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenylacetic acid → 3,5-Dibromo-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)phenylacetic acid

HRID 860971Notes

Reaction equation

HRID 860971 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([Br:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.I([Cl:28])(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([Br:20])[C:7]=1[O:8][C:9]1[CH:10]=[C:11]([CH:17]([CH3:19])[CH3:18])[C:12]([OH:15])=[C:13]([Cl:28])[CH:14]=1

Participants

4

Reactant 2

HCID 222558143,5-Dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenylacetic acidHCID 57347110Benyltrimethylammonium tetrachloroiodate

Product 1

HCID 693852043,5-Dibromo-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)phenylacetic acidYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 3,5-dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenylacetic acid (1.5 g, 3.4 mmol) in acetic acid (40 mL) at room temperature was added benzyltrimethylammonium tetrachloroiodate (1.42 g, 3.4 mmol). The reaction mixture was stirred for one hour and was filtered. The filtrate was concentrated, and the product was extracted with ethyl acetate, washed with saturated NaHCO3 (aq), NaCl (aq), and dried over MgSO4 and concentrated in vacuo. The residue was purified on column (silica gel, chloroform/methanol/acetic acid 98:2:0.3) to give 802 mg (50%) of 3,5-dibromo-4-(3-chloro-4-hydroxy-5-isopropylphenoxy)phenylacetic acid.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated
  3. extractionthe product was extracted with ethyl acetate
  4. washwashed with saturated NaHCO3 (aq), NaCl (aq)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on column (silica gel, chloroform/methanol/acetic acid 98:2:0.3)

Sources & evidence

ORD record
ord-99e72e913e4e44d8a75e7a78236b62ab
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

Loading…