2-Nitropropane → 2-Bromo-4-methyl4-nitropentanal

HRID 1790052Notes

Reaction equation

HRID 1790052 reaction equation
C(C=C)=O.[N+](C(C)C)([O-])=O.[CH3:11][C:12]([N+:18]([O-:20])=[O:19])([CH3:17])[CH2:13][CH2:14][CH:15]=[O:16].[Br:21]Br>C(O)(=O)C.O>[CH3:11][C:12]([N+:18]([O-:20])=[O:19])([CH3:17])[CH2:13][CH2:14][CH:15]=[O:16].[Br:21][CH:14]([CH2:13][C:12]([CH3:17])([N+:18]([O-:20])=[O:19])[CH3:11])[CH:15]=[O:16]

Participants

8

Reactant 4

HCID 3982-NitropropaneHCID 7847AcroleinHCID 24408BromineHCID 122640094-Methyl-4-nitrovaleraldehyde

Product 2

HCID 122640094-Methyl-4-nitrovaleraldehydeHCID 220385582-Bromo-4-methyl4-nitropentanalYield 163.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-Methyl-4-nitropentanal is prepared by condensation of acrolein and 2-nitropropane according to a known procedure (Synthesis 1986, 237). To a solution of 4-methyl-4-nitropentanal (8.5 g, 58.56 mmol) in acetic acid (125 ml) is added bromine (9.12 g, 57.07 mmol) dropwise while the temperature is kept below 15° C. After stirring for 15 minutes at room temperature the reaction is poured into a mixture of water and ice (250 ml) and extracted two times with dichloromethane. The combined organic extracts are washed with water and with brine, successively, dried over magnesium sulfate, and the solvent is removed under reduced pressure to leave 10.7 g of 2-bromo-4-methyl-4-nitropentanal which is used for the next step without further purification.

Workup

  1. customis kept below 15° C
  2. extractionextracted two times with dichloromethane
  3. washThe combined organic extracts are washed with water and with brine
  4. dry with materialsuccessively, dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-bcd96f282a0b42aebd3d55cb6b3b5052
Source dataset
uspto-grants-2006_07
Patent number
US07071208B2

Reaction notes

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