Hydrochloric Acid → HCID 69386720, compound

HRID 860970Notes

Reaction equation

HRID 860970 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22][CH3:23])=[C:15]([F:24])[CH:14]=2)=[C:7]([Br:25])[CH:6]=1.Cl>O1CCCC1.[OH-].[Li+]>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:26])=[O:2])[CH:6]=[C:7]([Br:25])[C:8]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:20])[CH3:21])[C:16]([O:22][CH3:23])=[C:15]([F:24])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69385839HCID 69385839, compound

Product 1

HCID 69386720HCID 69386720, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl[3,5-dibromo-4-(3-fluoro-5-isopropyl-4-methoxyphenoxy)phenyl]acetate (205 mg, 0.42 mmol) in tetrahydrofuran (30 mL), lithium hydroxide (30 mL, 1N) was added. The reaction mixture was stirred over night at room temperature, acidified with hydrochloric acid (1 N) and the aqueous and organic phase separated. The aqueous phase extracted with ethyl acetate. The combined organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on column (silica gel, chloroform/methanol/acetic acid 98:2:0.3) to give 210 mg (99%) of 3,5-dibromo-4-(3-fluoro-5-isopropyl-4-methoxyphenoxy)phenylacetic acid.

Workup

  1. customthe aqueous and organic phase separated
  2. extractionThe aqueous phase extracted with ethyl acetate
  3. washThe combined organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on column (silica gel, chloroform/methanol/acetic acid 98:2:0.3)

Sources & evidence

ORD record
ord-55f05e3c91e44795a3b152151d35cd32
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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