N-bromobutanimide → Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetate

HRID 1534564Notes

Reaction equation

HRID 1534564 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10].[Br:14]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3768392Methyl (2-methylphenyl)(oxo)acetate

Product 1

HCID 14697242Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetateYield 49.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5.34 g (30 millimoles) of methyl 2-methylphenylglyoxylate and 5.34 g (30 millimoles) of N-bromosuccinimide in 1,000 1 of tetrachloromethane are exposed for one hour to a 300 W Hg vapor lamp. Thereafter, the organic phase is washed once with water and three times with sodium bicarbonate solution and dried over sodium sulfate/sodium carbonate. After the organic phase has been evaporated down, the crude product is chromatographed over silica gel using 1:9 methyl tert-butyl ether/n-hexane. 3.8 g (49%) of the abovementioned compound are obtained as a yellow oil. 1H-NMR (CDCl3): δ=3.97 (s, 3H); 4.90 (s, 2H); 7.4-7.8 (m, 4H)

Workup

  1. washThereafter, the organic phase is washed once with water and three times with sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate/sodium carbonate
  3. customAfter the organic phase has been evaporated down
  4. customthe crude product is chromatographed over silica gel using 1:9 methyl tert-butyl ether/n-hexane

Sources & evidence

ORD record
ord-83b311347f1f4cc4a768319d2195eb4a
Source dataset
uspto-grants-1992_02
Patent number
US05089528

Reaction notes

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