Benzyl Bromide → HCID 15000227, compound

HRID 396122Notes

Reaction equation

HRID 396122 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5861374-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 15000227HCID 15000227, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.51 g (61.57 mmol) of potassium carbonate are added to a solution of 10.0 g (58.64 mmol) of 4-hydroxy-2-nitrobenzaldehyde in 70 ml of DMF. The solution is briefly stirred, then 10.53 g (61.57 mmol) of benzyl bromide are added and the reaction mixture is stirred at room temperature for 3 h. The resulting solid is then filtered off, 250 ml of water are added to the filtrate and the aqueous phase is extracted 3× with ethyl acetate. The organic phase is washed twice with water, dried over sodium sulphate, concentrated in vacuo and the residue is dried. 15.0 g (99%) of 4-benzyloxy-2-nitrobenzaldehyde are obtained as a yellow solid.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 3 h
  2. filtrationThe resulting solid is then filtered off
  3. addition250 ml of water are added to the filtrate
  4. extractionthe aqueous phase is extracted 3× with ethyl acetate
  5. washThe organic phase is washed twice with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customthe residue is dried

Sources & evidence

ORD record
ord-f540cf9a013244a58f7effce7f6193f4
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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