Phosphorus tribromide → Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-bromobutyrate

HRID 584001Notes

Reaction equation

HRID 584001 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12](O)[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1.P(Br)(Br)[Br:27]>O1CCOCC1>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]([Br:27])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 21964458Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-hydroxy-butyrate

Product 1

HCID 21964551Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-bromobutyrate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-hydroxy-butyrate (Step D) in dioxane, add phosphorous tribromide in dioxane dropwise. After stirring at room temperature for 16 hours, quench with water and chloroform. After few minutes, the reaction mixture can be neutralized by mild aqueous base, dry organic layer over Na2SO4, filter, concentrate and purify by flash chromatography on silica gel column (EtOAc:hex).

Workup

  1. customquench with water and chloroform
  2. waitAfter few minutes
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash chromatography on silica gel column (EtOAc:hex)

Sources & evidence

ORD record
ord-d85ae57fd17e4ec18423d12ab316ceb2
Source dataset
uspto-grants-2005_08
Patent number
US06924314B2

Reaction notes

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