Benzyl Alcohol → 2-(Benzyloxy)-3-bromo-5-chloropyridine

HRID 1959609Notes

Reaction equation

HRID 1959609 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5](Cl)=[N:6][CH:7]=[C:8]([Cl:10])[CH:9]=1.[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>CCCCCC.CN(C=O)C>[CH2:12]([O:19][C:5]1[C:4]([Br:3])=[CH:9][C:8]([Cl:10])=[CH:7][N:6]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 129015963-Bromo-2,5-dichloropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 220583822-(Benzyloxy)-3-bromo-5-chloropyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

In a microwave tube NaH (60% in paraffin. 56 mg. 1.4 mmol) was washed with hexane and 3-bromo-2,5-dichloro-pyridine (245 mg. 1.08 mmol) in dry DMF (2 mL) were added. To this suspension BnOH (123 μL. 1.23 mmol) in dry DMF (1 mL) was dropped carefully. The reaction mixture was stirred 15 min until the formation of hydrogen has ceased. The tube was sealed and stirred at 100° C. in a microwave reactor for 30 min. After removal of the solvent in vacuo the residue was partioned between water (10 mL) and DCM (10 mL) and extracted with DCM (3×10 mL). The combined organic fractions were washed with brine dried over Na2SO4 filtered and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. GC-MS (m/z): 297 [M+].

Workup

  1. additionwere added
  2. customThe tube was sealed
  3. customAfter removal of the solvent in vacuo the residue
  4. extractionextracted with DCM (3×10 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-b6e91a8632b34074ac8098c21b76bdf3
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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