2-Nitropropane → 3-Bromo-7-benzothiophene-carbaldehyde

HRID 974374Notes

Reaction equation

HRID 974374 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].[Br:8][C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH2:18]Br)[C:12]=2[S:11][CH:10]=1>C(O)C>[Br:8][C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH:18]=[O:2])[C:12]=2[S:11][CH:10]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 147805223-Bromo-7-bromomethylbenzothiophene

Product 1

HCID 199863443-Bromo-7-benzothiophene-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With stirring, 68.2 g (0.74 mole) of 2-nitropropane are added dropwise at room temperature, over a period of 45 minutes, to a Na-ethoxide solution prepared under an argon atmosphere from 14.2 g (0.61 mole) of sodium and 800 ml of abs. ethanol. 137 g (0.61 mole) of 3-bromo-7-bromomethylbenzothiophene are then added dropwise at room temperature, over a period of 1.5 hours, to the resulting white suspension. After the reaction mixture has been stirred for one day, the solvent is evaporated off from the reaction mixture in vacuo, the resulting residue of 101.2 g is dissolved in a mixture of hexane:diethyl ether 1:1 and the solution is purified by chromatography on silica gel. After evaporation of the solvent, 81 g (80% of the theoretical amount) of 3-bromo-7-benzothiophene-carbaldehyde are obtained as residue.

Workup

  1. stirringAfter the reaction mixture has been stirred for one day
  2. customthe solvent is evaporated off from the reaction mixture in vacuo
  3. dissolutionthe resulting residue of 101.2 g is dissolved in a mixture of hexane:diethyl ether 1:1
  4. customthe solution is purified by chromatography on silica gel
  5. customAfter evaporation of the solvent, 81 g (80% of the theoretical amount) of 3-bromo-7-benzothiophene-carbaldehyde
  6. customare obtained as residue

Sources & evidence

ORD record
ord-1ae22274ec364f248ee7d34599f174ce
Source dataset
uspto-grants-1991_11
Patent number
US05068359

Reaction notes

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