2-Nitropropane → 4-Bromo-2-fluorobenzaldehyde

HRID 1741841Notes

Reaction equation

HRID 1741841 reaction equation
[Na].[N+](C(C)C)([O-])=[O:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[C:11]([F:17])[CH:10]=1>C(O)C>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:3])=[C:11]([F:17])[CH:10]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 5360545Sodium

Product 1

HCID 1435174-Bromo-2-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (317 mg) was dissolved in ethanol (30 ml), then 2-nitropropane (1.24 ml) was added. To the mixture 4-bromo-2-fluorobenzyl bromide (3.55 g) in ethanol (10 ml) was added. The reaction mixture was stirred at room temperature for 3 hours, and insoluble materials were filtered off. The filtrate was concentrated and the residue was dissolved in diethyl ether and water. The organic layer was washed with 1N sodium hydroxide and water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (20:1) to give 4-bromo-2-fluorobenzaldehyde (2.28 g) as solid.

Workup

  1. filtrationinsoluble materials were filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe organic layer was washed with 1N sodium hydroxide and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel column
  8. washeluting with a mixture of hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-c8596b3a2db0413d807650b5f9d1c827
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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