Water → 4-(5-Bromopyridin-2-yl)cyclohexanone

HRID 1748522Notes

Reaction equation

HRID 1748522 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 866924705-Bromo-2-(1,4-dioxaspiro[4,5]decane-8-yl)pyridine

Product 1

HCID 866924654-(5-Bromopyridin-2-yl)cyclohexanoneYield 103%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-Bromo-2-(1,4-dioxaspiro[4,5]decane-8-yl)pyridine (9.0 g) described in Reference Example 102(2) was dissolved in trifluoroacetic acid (15 ml) and stirred at room temperature overnight. After completion of the reaction, water was added under ice cooling, neutralized by the addition of 4N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give 4-(5-bromopyridin-2-yl)cyclohexanone (7.9 g) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0b9aa11765f420b965e8a0d0d8b7c74
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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