N-bromobutanimide → HCID 12519668, compound

HRID 128761Notes

Reaction equation

HRID 128761 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([CH3:22])[CH2:15][O:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:12][CH2:11]1>C(Cl)(Cl)(Cl)Cl>[C:13]([O:12][CH2:11][C:10]([CH3:9])([CH3:22])[CH2:15][Br:1])(=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 698951,3-Dioxane, 5,5-dimethyl-2-phenyl-

Product 1

HCID 12519668HCID 12519668, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
24 °C

Procedure

N-Bromosuccinimide (20.7 g) was added to a stirred solution of 5,5-dimethyl-2-phenyl-1,3-dioxane (19.2 g) in 200 mL of CCl4 containing 8.5 g of BaCO3 in suspension. The mixture was heated to reflux under Ar for 2.2 h, then cooled to 24° C. over 15 h, filtered and concentrated. The residue was partitioned between ether and water, and the ethereal solution was washed with brine, dried (MgSO4), filtered and concentrated to give 24.8 g of a yellow oil which was stored in the dark at 0° C. under Ar.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under Ar for 2.2 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was partitioned between ether and water
  6. washthe ethereal solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9ff2ce903855441da192bfb16b41f434
Source dataset
uspto-grants-1995_11
Patent number
US05464866

Reaction notes

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