Benzyl Bromide → 3-(Benzyloxy)-5-chloro-2-nitropyridine

HRID 1426164Notes

Reaction equation

HRID 1426164 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:15][C:16]1[CH:17]=[C:18]([OH:25])[C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=1>CN(C=O)C>[CH2:2]([O:25][C:18]1[C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=[C:16]([Cl:15])[CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 187656985-Chloro-2-nitropyridin-3-ol

Product 1

HCID 673694373-(Benzyloxy)-5-chloro-2-nitropyridineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(Bromomethyl)benzene (7.905 ml, 66.46 mmol) was added to a mixture of cesium carbonate (21.65 g, 66.46 mmol) and 5-chloro-2-nitropyridin-3-ol (11.6 g, 66.46 mmol) in DMF (50 mL). The reaction mixture was stirred overnight at ambient temperature, then partitioned between ethyl acetate and water, washed with water and brine, dried, and concentrated to afford 3-(benzyloxy)-5-chloro-2-nitropyridine (16.0 g, 91.0% yield) as a light yellow powder. 1H NMR (CDCl3) δ 5.25 (s, 2H), 7.41 (m, 5H), 7.53 (s, 1H), 8.04 (s, 1H).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7fa26f5191db426f9ea470beb4b8f849
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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