Benzyl Bromide → 4-(Benzyloxy)-2-bromopyridine

HRID 404162Notes

Reaction equation

HRID 404162 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][N:5]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOC(C)=O>CN(C=O)C>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([Br:3])[CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178516474HCID 178516474, compound

Product 1

HCID 153891994-(Benzyloxy)-2-bromopyridineYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (761 mg, 19.83 mmol) was added portion wise to 2-bromo-4-hydroxypyridine (3 g, 17.24 mmol) in DMF (50 mL) at 0° C. under Ar(g). Then the reaction mixture was stirred at it for 10 min after which it was again cooled down at 0° C. and benzyl bromide (2.15 mL, 18.10 mmol) was added. The reaction was stirred at it for 4 h, after which it was poured onto brine (200 mL) and EtOAc (200 mL) was added. The phases were separated and the organic phase was dried over MgSO4, filtered and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 to 80:20) to furnish I as a white solid (2.331 g, 51%).

Workup

  1. stirringThe reaction was stirred at it for 4 h
  2. additionwas added
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customsubsequently evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting with hexane/EtOAc (90:10 to 80:20)

Sources & evidence

ORD record
ord-78c9405db4494b47962b57e096821ad5
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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