Benzyl Bromide → HCID 12111719, compound

HRID 1642634Notes

Reaction equation

HRID 1642634 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH:13]=[O:14].C([O-])([O-])=O.[K+].[K+]>O>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 12111719HCID 12111719, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of benzyl bromide (6.9 g, 40.3 mmol) and 3-hydroxy-4-nitrobenzaldehyde (9.7 g, 58.0 mmol) is added K2CO3 (8.9 g, 64.4 mmol). The mixture is stirred at ambient temperature overnight, diluted with water and extracted with EtOAc. The organic phase is washed with aqueous K2CO3 and brine, dried over MgSO4, filtered and concentrated to afford 3-benzyloxy-4-nitrobenzaldehyde as a yellow solid: MS (M+H)+=258.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with aqueous K2CO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bc8ed470fa644b76912b2e450ab1fffd
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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