Potassium tert-butoxide → 5-(3-Bromophenyl)-5-methylmorpholin-3-one

HRID 221663Notes

Reaction equation

HRID 221663 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58155284N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide

Product 1

HCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The crude N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (70 g, 230 mmol) was dissolved in tert-butanol (1 l). The solution was treated with portions of potassium tert-butoxide (52 g, 460 mmol). The mixture was refluxed for 30 min, after cooling quenched with water and evaporated. The residue was dissolved in EtOAc (500 ml) and washed with water and brine. The organic phase was dried with Na2SO4 and concentrated in vacuo to yield the crude title compound. The crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1) to give the title compound in the form of a grey solid. 1H-NMR (400 MHz, DMSO-d6): 8.66 (s, 1H), 7.60 (s, 1H), 7.48 (d, 1H), 7.44 (d, 1H), 7.34 (t, 1H), 4.02 (s, 2H), 3.92 (d, 1H), 3.68 (d, 1H), 1.38 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. temperatureafter cooling
  3. customquenched with water
  4. customevaporated
  5. dissolutionThe residue was dissolved in EtOAc (500 ml)
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto yield the crude title compound
  10. customThe crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1)

Sources & evidence

ORD record
ord-086b51c2fe8b40fb9c46b7832f05b789
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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