Benzyl Bromide → 4-(Benzyloxy)-3-methoxy-2-nitrobenzaldehyde

HRID 339760Notes

Reaction equation

HRID 339760 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

Product 1

HCID 5618174-(Benzyloxy)-3-methoxy-2-nitrobenzaldehydeYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (155 g, 786 mmol) was dissolved in DMF (1500 mL) and the stirred solution was treated with potassium carbonate (217 g, 1.57 mol) followed by benzyl bromide (161 g, 0.94 mol). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and separated between water (2 L) and EtOAc (2 L). The organic layer was washed with a saturated sodium chloride solution (3×2 L), dried (anh. sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with Et2O (1 L) to give 4-(benzyloxy)-3-methoxy-2-nitrobenzaldehyde (220 g, 97%): 1H NMR (DMSO-d6) δ: 9.77 (1H, s), 7.87 (1H, d), 7.58 (1H, d), 7.51 (1H, m), 7.49 (1H, m), 7.39 (3H, m), 5.36 (2H, s), 3.05 (3H, s).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customseparated between water (2 L) and EtOAc (2 L)
  3. washThe organic layer was washed with a saturated sodium chloride solution (3×2 L)
  4. dry with materialdried (anh. sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solids were triturated with Et2O (1 L)

Sources & evidence

ORD record
ord-09ff7b9f0a514800a333723e46c98762
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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