3,5-Dibromopyridine → 1432621-15-2

HRID 712691Notes

Reaction equation

HRID 712691 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[O:9]1[CH2:12][C:11](=[O:13])[CH2:10]1>C1COCC1>[Br:8][C:6]1[CH:7]=[C:2]([C:11]2([OH:13])[CH2:12][O:9][CH2:10]2)[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 693693,5-DibromopyridineHCID 150242543-Oxetanone

Product 1

HCID 754066851432621-15-2Yield 27.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a cooled (−20° C.) solution of 3,5-dibromopyridine (1.2 g, 5.0 mmol) in THF (2 mL) is added a solution of isopropylmagnesium chloride-lithium chloride complex in THF (1.7 M, 2.9 mL, 4.9 mmol). The resultant mixture is stirred warming to −10° C. for 30 min. The mixture is recooled to −20° C. and 3-oxetanone (432 mg, 6.0 mmol) is added. After stirring for 1 h, the reaction is quenched with saturated aqueous ammonium chloride solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. Purification by silica gel column (0-10% MeOH in DCM) provided 3-(5-bromo-pyridin-3-yl)-oxetan-3-ol (320 mg).

Workup

  1. customis recooled to −20° C.
  2. customthe reaction is quenched with saturated aqueous ammonium chloride solution
  3. extractionis extracted with EtOAc
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel column (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-3457bbaaab984eaca44ca725d938c04b
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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