Water → 5-(3-Bromophenyl)-5-(difluoromethyl)-3-morpholinone

HRID 81538Notes

Reaction equation

HRID 81538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:14][C:15](=[O:18])[CH2:16]Cl)([CH2:12][OH:13])[CH:9]([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:9]([F:11])[F:10])[NH:14][C:15](=[O:18])[CH2:16][O:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66665688N-[1-(3-Bromo-phenyl)-2,2-difluoro-1-hydroxymethyl-ethyl]-2-chloro-acetamide

Product 1

HCID 666654075-(3-Bromophenyl)-5-(difluoromethyl)-3-morpholinone

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

N-[1-(3-Bromo-phenyl)-2,2-difluoro-1-hydroxymethyl-ethyl]-2-chloro-acetamide (8.10 g, 23.65 mmol) and potassium tert-butoxide (5.31 g, 47.3 mmol) were heated to 95° C. in 118 ml tert-butanol for 30 minutes. After completion water was added and the reaction was evaporated. The residue was put between ethyl acetate and water. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The organic phases were washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure to yield the title compound as off-white solid. 1H-NMR (360 MHz, DMSO-d6): 9.13 (s, 1H, NH), 7.78 (s, 1H), 7.59 (m, 2H), 7.42 (t, 1H), 6.48 (t, 1H, CHF2), 4.28 (d, 1H), 4.10 (m, 2H), 3.92 (m, 1H); MS: 306 [(M+H)+].

Workup

  1. customthe reaction was evaporated
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washThe organic phases were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9de3893246ff41f68a007dde26a99f40
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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