Acetone → HCID 67155071, compound

HRID 712723Notes

Reaction equation

HRID 712723 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C(NC(C)C)(C)C.[Li].[CH3:17][C:18]([CH3:20])=[O:19]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:8])[C:7]=1[C:18]([OH:19])([CH3:20])[CH3:17]

Participants

6

Reactant 3

HCID 180AcetoneHCID 8202063-Bromo-5-fluoropyridineHCID 45051747Lithium diisopropylamine

Product 1

HCID 67155071HCID 67155071, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask is added 3-bromo-5-fluoropyridine (475 mg, 2.7 mmol) in 4 ml of dry THF at −78° C., followed by the addition of lithium diisopropylamine (1.6 ml, 3.2 mmol). The reaction mixture is stirred at −78° C. for 1 hour, followed by the addition of acetone (0.6 ml). The reaction mixture is warmed up and stirred at room temperature for 30 minutes. The reaction mixture is diluted with EtOAc, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 190 mg of 2-(3-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol.

Workup

  1. temperatureThe reaction mixture is warmed up
  2. stirringstirred at room temperature for 30 minutes
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-ac6fc5b030044adc8a2238aba5fed78e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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