Diazomethane → 5-Bromo-1-diazo-3-(3,4-dichlorophenyl)-2-pentanone

HRID 357246Notes

Reaction equation

HRID 357246 reaction equation
[N+:1](=[CH2:3])=[N-:2].CN(N=O)/C(/N)=N/[N+]([O-])=O.[OH-].[K+].[Br:16][CH2:17][CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[C:20](Cl)=[O:21]>CCOCC>[Br:16][CH2:17][CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[C:20](=[O:21])[CH:3]=[N+:1]=[N-:2]

Participants

6

Reactant 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 95620601-Methyl-2-nitro-1-nitrosoguanidineHCID 54519315alpha-(2-Bromoethyl)-3,4-dichlorophenylacetic acid chloride

Product 1

HCID 537812765-Bromo-1-diazo-3-(3,4-dichlorophenyl)-2-pentanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Prepare a solution of diazomethane from 15 g of MNNG by reaction with 45 ml of 40% aqueous KOH topped with 150 ml. of Et2O and cool in an ice bath. Add an Et2O solution (40 ml.) of the product of Step 3 (8.2 g, 5 24.8 mmoles) in small volumes, stir the solution in the ice bath for 15 min, then heat to reflux for 30 min. Remove the solvent in vacuo. Purify the resulting mixture by flash chromatography on silica gel using CH2Cl2 as eluent. Yield: 7.0 g (IR: 2100 cm-1, 1630 cm-1).

Workup

  1. temperatureheat
  2. temperatureto reflux for 30 min
  3. customRemove the solvent in vacuo
  4. customPurify the resulting mixture by flash chromatography on silica gel

Sources & evidence

ORD record
ord-de8b5c7df0224edabc56be3a57f66237
Source dataset
uspto-grants-1998_11
Patent number
US05840725

Reaction notes

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