Hydrochloric Acid → 2-(4-Bromophenyl)-2-methylpropanoic acid

HRID 896712Notes

Reaction equation

HRID 896712 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.C[Si](C)(C)[O-].[K+].Cl>C1COCC1.O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 109336792-(4-Bromophenyl)-2-methylpropanoic acidYield 101.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-bromophenyl)-2-methylpropanoate (3.75 g, 14.6 mmol, prepared according to J. Org. Chem., 59:2620-2622(1994)) in 150 mL of THF was allowed to react with potassium trimethylsilanolate (2.62 g, 20.4 mmol) at ambient temperature, for 60 hours, with continuous stirring. The reaction was then diluted with water and DCM. The pH of the aqueous phase was then adjusted to ca. 4, using 1M HCl. The aqueous layer was then extracted three times with additional DCM. The organic layers were pooled, dried over sodium sulfate, filtered and then concentrated to obtain 3.59 g of 2-(4-bromophenyl)-2-methylpropanoic acid, as a white solid, which gave LC/MS and proton NMR spectra consistent with theory.

Workup

  1. extractionThe aqueous layer was then extracted three times with additional DCM
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42b0688ed54f445696fa4fb32e2ef1b7
Source dataset
uspto-grants-2005_07
Patent number
US06919343B2

Reaction notes

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