Acetic Acid → Methyl 2-(3-bromophenyl)-2-methylpropanoate

HRID 1058586Notes

Reaction equation

HRID 1058586 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)([CH3:5])[C:3]#N.[C:13](O)(=[O:15])C.S(=O)(=O)(O)[OH:18]>O>[CH3:13][O:15][C:3](=[O:18])[C:2]([CH3:5])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 105132942-(3-Bromophenyl)-2-methylpropanenitrile

Product 1

HCID 24777892Methyl 2-(3-bromophenyl)-2-methylpropanoateYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-Methyl-2-[3-bromophenyl]propionitrile (0.56 g, 2.5 mmol) was refluxed in sulfuric acid (2 ml), water (3 ml) and acetic acid (2.5 ml) overnight. The reaction mixture was poured in water, then extracted with Et2O. The combined organic extracts were dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 10% EtOAc, 1% HOAc) to give the title compound as a white solid (0.2 g, 36%), which was converted to the methyl ester with diazo methane in Et2O and was used in the next reaction without further purification.

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe combined organic extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 10% EtOAc, 1% HOAc)

Sources & evidence

ORD record
ord-df668ddbcaab49bf9e906604c82bfd38
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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