4-Bromophenol → Methyl 3-(4-bromophenoxy)-3-phenyl-2-hydroxybutyrate

HRID 378362Notes

Reaction equation

HRID 378362 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1([C:15]2([CH3:22])[O:21][CH:16]2[C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)([CH3:22])[CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78084-BromophenolHCID 228011Methyl 3-methyl-3-phenyloxirane-2-carboxylate

Product 1

HCID 15292297Methyl 3-(4-bromophenoxy)-3-phenyl-2-hydroxybutyrateYield 20%

Procedure

51.9 g (0.3 mol) of 4-bromophenol and 19.2 g (0.1 mol) of methyl 3-phenyl-2,3-epoxybutyrate are stirred at 100° C. for 8 hours and at room temperature for 12 hour. After removal of the excess phenol by distillation, the residue is purified by flash chromatography (silica gel, n-hexane/ethyl acetate 9:1) to result in 7.2 g of a white solid.

Workup

  1. customAfter removal of the excess phenol
  2. distillationby distillation
  3. customthe residue is purified by flash chromatography (silica gel, n-hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-d9675b544e26491989ee50b08f760dbe
Source dataset
uspto-grants-2000_02
Patent number
US06030975

Reaction notes

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