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

HRID 251566Notes

Reaction equation

HRID 251566 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-9ac3e6b40b63439c85cd296fe2fdea96
Source dataset
uspto-grants-2011_01
Patent number
US07863475B2

Reaction notes

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