Hydrogen Bromide → HCID 18625989, compound

HRID 1860066Notes

Reaction equation

HRID 1860066 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.Br>C(O)(=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:24][CH:25]=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

A solution of ethyl 3-(4-benzyloxyphenyl)-2-(4-fluorophenoxy)propionate (7.00 g), which is the product of Reference example 37(a) in a solution of hydrogen bromide in acetic acid (25%, 70 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. Potassium carbonate (6.90 g) was added to a solution of the residue in ethanol (70 ml). This mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=9/1-4/1 as the eluant to afford the desired compound (2.75 g) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionPotassium carbonate (6.90 g) was added to a solution of the residue in ethanol (70 ml)
  3. stirringThis mixture was stirred at ambient temperature for 4 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate and water
  6. customthe layers were separated
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-f981d014686e4450ad7e23a0d1f39e17
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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