Sodium Thiosulfate → 4-Bromo-2,6-diisopropylaniline

HRID 1698417Notes

Reaction equation

HRID 1698417 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH:55]([C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([CH:64]([CH3:66])[CH3:65])[C:59]=1[NH2:67])([CH3:57])[CH3:56].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Br:1][C:62]1[CH:63]=[C:58]([CH:55]([CH3:57])[CH3:56])[C:59]([NH2:67])=[C:60]([CH:64]([CH3:66])[CH3:65])[CH:61]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 32484DiisopropylanilineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 117801144-Bromo-2,6-diisopropylanilineYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40.8 g (85 mmol) of tetra-n-butylammonium tribromide are added, at 0° C. and portionwise, to a solution of 15 g (85 mmol) of 2,6-diisopropylphenyl-amine in 200 ml of tetrahydrofuran. The medium is stirred for 2 h. It is then poured into a saturated aqueous solution of sodium thiosulphate and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulphate. The residue is purified by silica gel chromatography (80/20 heptane/ethyl acetate). 20.6 g of 4-bromo-2,6-diisopropylphenylamine are obtained in the form of a yellow oil (yield=95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThey are dried over sodium sulphate
  4. customThe residue is purified by silica gel chromatography (80/20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5dc0bee2285b47c4a31114c8d21bdcd5
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

Loading…