Hydrogen Bromide → Methyl 2-(2,6-Dipropyl-4-Bromomethyl-Phenoxy)Phenylacetate

HRID 37239Notes

Reaction equation

HRID 37239 reaction equation
[CH2:1]([C:4]1[CH:21]=[C:20]([CH2:22]O)[CH:19]=[C:18]([CH2:24][CH2:25][CH3:26])[C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH3:3].P(Br)(Br)[Br:28].Br>C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:4]1[CH:21]=[C:20]([CH2:22][Br:28])[CH:19]=[C:18]([CH2:24][CH2:25][CH3:26])[C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24614Phosphorus tribromideHCID 19934855HCID 19934855, compound

Product 1

HCID 19934848Methyl 2-(2,6-Dipropyl-4-Bromomethyl-Phenoxy)Phenylacetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2.66.1 g (7.46 mmol) of the product of Step A dissolved in 15 mL of carbon tetrachloride was added 0.709 mL (7.47 mmol) of phosphorous tribromide and the reaction mixture was magnetically stirred at room temperature for 30 min as hydrogen bromide was evolved. The magnetic stir bar was removed, and the reaction mixture was concentrated in vacuo. The residue was redissolved and evaporated from carbon tetrachloride several times to remove most of the hydrogen bromide. Finally, the residue was purified by rapid flash chromatography on a silica gel column eluted with 10% EtOAc-hexane. Combination and evaporation of the purified fractions and drying in vacuo afforded 2.129 (68%) of the title compound which was used directly in the next step without further characterization.

Workup

  1. customThe magnetic stir bar was removed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was redissolved
  4. customevaporated from carbon tetrachloride several times
  5. customto remove most of the hydrogen bromide
  6. customFinally, the residue was purified by rapid flash chromatography on a silica gel column
  7. washeluted with 10% EtOAc-hexane
  8. customCombination and evaporation of the purified fractions
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-daa34a8c96b44fc1ac20a4442935256e
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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