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

HRID 1259494Notes

Reaction equation

HRID 1259494 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 brine (3×2 L), dried (sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with Et2O (1 L) to give the title compound (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 brine (3×2 L)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solids were triturated with Et2O (1 L)

Sources & evidence

ORD record
ord-c19e7db332704d4d8b0c6e037a90918f
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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