Ethanol → Ethyl 2-(3-bromophenyl)-2-methylpropanoate

HRID 2377455Notes

Reaction equation

HRID 2377455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:14].[CH2:18]([OH:20])[CH3:19]>O>[CH2:18]([O:20][C:9](=[O:14])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:12])[CH3:11])[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 105132942-(3-Bromophenyl)-2-methylpropanenitrile

Product 1

HCID 12805127Ethyl 2-(3-bromophenyl)-2-methylpropanoateYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(3-bromo-phenyl)-2-methyl-propionitrile (prepared as described by Barlaam et al. J. Med. Chem., 1999, 42, 23, 4890-4908 incorporated herein by reference; 1.4 g, 6.24 mmol) was dissolved in ethanol (40 mL), treated with concentrated sulfuric acid (1 mL) and the resulting reaction mixture was refluxed for 36 h. The reaction mixture was cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title product as an orange oil (0.77 g, 46%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 36 h
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-0d32ee781b124467a107678101196a15
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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