1-Nitropropane → 4-Fluoro-3-phenoxybenzaldehyde

HRID 1835036Notes

Reaction equation

HRID 1835036 reaction equation
[Na].[N+](CCC)([O-])=[O:3].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1>C(O)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[O:3])=[CH:11][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 79031-NitropropaneHCID 5360545SodiumHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 1100684-Fluoro-3-phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving sodium metal (0.41 g, 17.8 g-atom) in ethanol (25 ml), nitropropane (1.65 g) and 4-(bromomethyl)-1-fluoro-2-phenoxybenzene (5.00 g) are added and the mixture stirred for 3.5 h. The reaction was filtered and concentrated in vacuo. The residue is taken up in ether and washed with water (10 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (10:90) to afford the title compound as a colorless liquid which is characterized by 1HNMR spectral analyses.

Workup

  1. additionare added
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated in vacuo
  4. washwashed with water (10 ml)
  5. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel eluting with ether:hexane (10:90)

Sources & evidence

ORD record
ord-67fa4ed800e946ee9b846e76e346d5f3
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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