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

HRID 1911633Notes

Reaction equation

HRID 1911633 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-dac400408d654b64b0c7194fe826f8c4
Source dataset
uspto-grants-2013_12
Patent number
US08604083B2

Reaction notes

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