Tetra-n-butylammonium tribromide → HCID 58764135, compound

HRID 859635Notes

Reaction equation

HRID 859635 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:55]([O:57][C:58]1[CH:59]=[CH:60][C:61]([CH2:65][CH3:66])=[C:62]([OH:64])[CH:63]=1)[CH3:56]>C(Cl)(Cl)Cl>[Br:1][C:59]1[C:58]([O:57][CH2:55][CH3:56])=[CH:63][C:62]([OH:64])=[C:61]([CH2:65][CH3:66])[CH:60]=1

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 58764267HCID 58764267, compound

Product 1

HCID 58764135HCID 58764135, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of tetrabutyl ammonium tribromide (9.9 g, 20.5 mmol) in CHCl3 (60 mL) was added to a stirred solution of 5-ethoxy-2-ethyl-phenol (3.1 g, 18.6 mmol) dissolved in CHCl3 (90 mL). The reaction mixture was stirred for 30 mins and then quenched with 5% solution of sodium thiosulfate (30 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1 N HCl, brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as an oil (2.6 g, 58%).

Workup

  1. customquenched with 5% solution of sodium thiosulfate (30 mL)
  2. stirringThe biphasic mixture was stirred for 30 mins
  3. customthe layers were separated
  4. washThe organic layer was washed with 1 N HCl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a red oil
  7. customPurification by flash column chromatography (0% to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b34b3d08a76642fea68bbd0724c3bd0a
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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