Hydrochloric Acid → (+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 533500Notes

Reaction equation

HRID 533500 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([O:15]CC)=[O:14])=[CH:6][CH:5]=1.Cl>C1COCC1.CO.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 56950323Ethyl 4-(4-bromophenyl)-2-methanesulfonyl-2-methylbutanoate

Product 1

HCID 66577906(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Lithium hydroxide (3.29 g, 78.5 mmol) was added to a stirred solution of (+/−)-ethyl 4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.50 g, 78.5 mmol) in THF:MeOH:water (2:2:1, 225 mL) at 0° C. The reaction was warmed to room temperature as the ice bath expired. After 18 hours the reaction was acidified to pH 4 with 1N HCl (aq) and extracted with ethyl acetate (2×). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give a white solid (8.5 g, 97%). LCMS m/z 333.1 (M−1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (s, 3H) 1.95-2.05 (m, 1H) 2.30-2.48 (m, 2H) 2.67-2.79 (m, 1H) 3.10 (s, 3H) 3.26 (br. s., 1H) 7.17-7.24 (m, 2H) 7.43-7.52 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60d917c91a70410bba79facf0576c2be
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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