Acetic Acid → 3-(4-Bromophenyl)-3-o-tolylpropanoic acid

HRID 1527962Notes

Reaction equation

HRID 1527962 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH:14](C#N)[C:15]([O:17]CC)=[O:16])=[CH:9][CH:8]=1.C(O)(=O)C>C(OCC)(=O)C>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 67015643Ethyl 3-(4-bromophenyl)-2-cyano-3-o-tolylpropanoate

Product 1

HCID 670156223-(4-Bromophenyl)-3-o-tolylpropanoic acidYield 21.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sulfuric acid (940 g, 9.59 mol) was added over 30 min under ice cooling to a mixture of ethyl 3-(4-bromophenyl)-2-cyano-3-o-tolylpropanoate (200 g, 494 mmol) in acetic acid (1.06 kg, 17.7 mol), while keeping the internal temperature below 27° C., then the reaction mixture was heated at reflux for 20 h. After cooling to 40° C. ice (500 g) and ethyl acetate (1500 mL) were added, the precipitate collected by filtration and washed with water to produce the title compound (34.5 g). The filtrate was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was stored in the refrigerator for 1 h. Then the precipitate was collected by filtration and washed with acetic acid and heptane to afford a second crop of product (96.2 g). Total yield: 130.7 g (83%). Off-white solid, MS: 319.0 [M−H]−.

Workup

  1. customthe internal temperature below 27° C.
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 20 h
  4. additionwere added
  5. filtrationthe precipitate collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-6e7de0c5112c4c35bf703cf39c82d7bd
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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