Hydrogen Bromide → HCID 18625989, compound

HRID 1268963Notes

Reaction equation

HRID 1268963 reaction equation
Br.C([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=1)C1C=CC=CC=1>C(O)(=O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 18625833HCID 18625833, compound

Product 1

HCID 18625989HCID 18625989, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a hydrogen bromide.acetic acid solution (25%, 70 ml) was added ethyl 3-(4-benzyloxyphenyl)-2-(4-fluorophenoxy)propionate (7.00 g) obtained from Reference example 25(a), and the reaction solution was stirred for 3 hours at room temperature. The reaction solution was concentrated under reduced pressure, then the residue was dissolved in ethanol (70 ml), and potassium carbonate (6.90 g) was added thereto followed by stirring for 4 hours at room temperature. The reaction solution was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The separated ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel-column (eluant; hexane/ethyl acetate=9/1˜4/1) to give the target compound (2.75 g) as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (70 ml)
  3. additionpotassium carbonate (6.90 g) was added
  4. stirringby stirring for 4 hours at room temperature
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue was partitioned between ethyl acetate and water
  7. dry with materialThe separated ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel-column (eluant; hexane/ethyl acetate=9/1˜4/1)

Sources & evidence

ORD record
ord-0bce9b48161f4e8da3f9e1561e77fcc1
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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