N-bromobutanimide → Methyl 2-bromo-2-(4-methoxyphenyl)acetate

HRID 254448Notes

Reaction equation

HRID 254448 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.Br>[Br:21][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90266Methyl 4-methoxyphenylacetate

Product 1

HCID 10753737Methyl 2-bromo-2-(4-methoxyphenyl)acetateYield 101.8%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of methyl 4-methoxyphenylacetate (20 g, 0.11 mol) and NBS (0.11 mol) in CCl4 (0.2 l) were added 3 drops of 48% HBr and this mixture was heated to reflux for 8 h. The cooled solution was filtered through a pad of silica gel and the filtrate was evaporated in vacuo to give 29 g of the title compound as pale yellow oil, which was used in the subsequent step without further purification.

Workup

  1. temperaturethis mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationThe cooled solution was filtered through a pad of silica gel
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-271dd77ef305423cbc4d7f21ae0cc4a8
Source dataset
uspto-grants-2011_01
Patent number
US07875643B2

Reaction notes

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