N-bromobutanimide → Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetate

HRID 550840Notes

Reaction equation

HRID 550840 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.[Br:16]N1C(=O)CCC1=O>Br.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[CH:4]([Br:16])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:14])[F:13])[CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetate

Product 1

HCID 19796654Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetateYield 39%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (3-trifluoromethyl-phenyl)-acetic acid methyl ester (6.0 g, 25.9 mmol) and N-bromosuccinimide (9.2 g, 51.7 mmol) and a few drops of hydrobromic acid (48% solution) in chloroform (250 mL) was heated under reflux for two days. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 5% ethyl acetate/hexanes gave Bromo-(3-trifluoromethyl-phenyl)-acetic acid methyl ester (3.0 g, 39% yield) as colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two days
  3. concentrationThe reaction mixture was concentrated to dryness
  4. washElution with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3fd6d3e91d3544559763996e048f6d18
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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