Water → 3-Bromo-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

HRID 452215Notes

Reaction equation

HRID 452215 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F.O>CN(C=O)C.C1CCCCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3](=[O:8])[N:4]([C:17]2[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[Cl:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 8185493-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 595365983-Bromo-1-(2-chloro-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

2.00 g (11.5 mmol) of 3-bromopyridin-2(1H)-one (O, S. Tee, M. Pavent, J. Am. Chem. Soc. 1982, 104, 4142-4146) are dissolved in 40 ml of DMF. The mixture is cooled to 0° C., and 2.04 g (17.2 mmol, 95% strength) of potassium tert-butoxide are added. After about 15 min, the ice bath is removed, and after a further 30 min, 2.22 g (12.6 mmol) of 2-chloro-1-fluoro-4-nitrobenzene are added. The mixture is stirred at RT for 4 h. The mixture is then added to water and extracted three times with ethyl acetate. The combined organic phases are shaken with saturated sodium chloride solution and dried over sodium sulphate. The solvent is removed under reduced pressure, and the residue is suspended in pentane and filtered off with suction. The solid obtained is boiled with cyclohexane/ethyl acetate 10:1. The product is filtered off with suction and washed with cyclohexane/ethyl acetate 10:1. This gives 2.54 g (67% of theory) of the desired compound.

Workup

  1. customthe ice bath is removed
  2. waitafter a further 30 min
  3. extractionextracted three times with ethyl acetate
  4. stirringThe combined organic phases are shaken with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customThe solvent is removed under reduced pressure
  7. filtrationfiltered off with suction
  8. customThe solid obtained
  9. filtrationThe product is filtered off with suction
  10. washwashed with cyclohexane/ethyl acetate 10:1

Sources & evidence

ORD record
ord-28751dc36e8c4f3fa9d61cb5053aa424
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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