Water → 3-Bromo-2-(4-chloro-3-trifluoromethyl-phenoxy)-4-methyl-5-nitro-pyridine

HRID 508486Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:9](Cl)=[N:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[CH3:14].O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29]>CC(CC)=O>[Br:7][C:8]1[C:9]([O:27][C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:23]=2)=[N:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 250 ml three-necked round-bottomed flask, 4.00 g 4-chloro-3-trifluoromethyl-phenol is dissolved in 80 ml of dry methyl-ethyl-ketone. 3.85 g potassium carbonate followed by 4.70 g of 3-bromo-2-chloro-4-methyl-5-nitro-pyridine are added. The resulting brown suspension is heated to 80° C. under stirring for 3 hours. Afterwards, the green suspension is allowed to reach an ambient temperature and it then poured into water. The mixture is extracted with ethyl actetate (3×50 ml). The combined organic phases are washed with brine, dried over sodium sulfate, filtered and the solvent removed in vacuo. After purification of the raw product on silica gel with cyclohexane/ethyl actetae 19:1 (v:v) 7.36 g of the title compound are obtained as a light yellow gum that solidifies upon standing (MP: 73-74° C.).

Workup

additionare added
customto reach an ambient temperature
extractionThe mixture is extracted with ethyl actetate (3×50 ml)
washThe combined organic phases are washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent removed in vacuo
customAfter purification of the raw product on silica gel with cyclohexane/ethyl actetae 19:1 (v:v) 7.36 g of the title compound
customare obtained as a light yellow gum

Sources & evidence

ORD record: ord-3af990aea8ca4752b2dd750a1a04ac40
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096525B2

Reaction notes

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