2-Bromoethanol → 2-Methyl-2-(4-nitrophenyl)-propionic acid, 2-bromo-ethyl ester

HRID 1910760Notes

Reaction equation

HRID 1910760 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])[C:7]([OH:9])=[O:8].[Br:20][CH2:21][CH2:22]O>C(#N)C>[CH3:10][C:6]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([CH3:5])[C:7]([O:9][CH2:22][CH2:21][Br:20])=[O:8]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 24386Thionyl ChlorideHCID 7818982-Methyl-2-(4-nitrophenyl)propanoic acid

Product 1

HCID 673269282-Methyl-2-(4-nitrophenyl)-propionic acid, 2-bromo-ethyl esterYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Thionyl chloride (3 mL, 41 mmol) was added to 2-methyl-2-(4-nitrophenyl)-propionic acid (1 g, 4.78 mmol) and heated at 90° C. overnight. Excess thionyl chloride was evaporated to give a crude acid chloride which was dissolved in acetonitrile (8 mL). To this was added 2-bromoethanol (0.41 mL, 5.78 mmol) then the mixture was heated at reflux overnight. After concentration in vacuo, the residue was diluted with ethyl acetate and washed with sodium bicarbonate solution, then the organic layer was dried and evaporated to afford 2-methyl-2-(4-nitrophenyl)-propionic acid, 2-bromo-ethyl ester (0.99 g, 65.5%).

Workup

  1. customExcess thionyl chloride was evaporated
  2. customto give a crude acid chloride which
  3. temperaturethe mixture was heated
  4. temperatureat reflux overnight
  5. concentrationAfter concentration in vacuo
  6. additionthe residue was diluted with ethyl acetate
  7. washwashed with sodium bicarbonate solution
  8. customthe organic layer was dried
  9. customevaporated

Sources & evidence

ORD record
ord-57b7a2bf535c40e88d58c5c3f21991d3
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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