Lithium Hydroxide → 4-(4-Bromo-2-fluoro-phenyl)-2-methanesulfonyl-2-methyl-butyric acid

HRID 533520Notes

Reaction equation

HRID 533520 reaction equation
BrC1C=CC(CCC(C)(S(C)(=O)=O)C(O)=O)=CC=1.C([O:21][C:22](=[O:39])[C:23]([S:35]([CH3:38])(=[O:37])=[O:36])([CH3:34])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=1[F:33])C.[OH-].[Li+]>O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][C:23]([S:35]([CH3:38])(=[O:36])=[O:37])([CH3:34])[C:22]([OH:39])=[O:21])=[C:27]([F:33])[CH:28]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 66577906(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acidHCID 665779254-(4-Bromo-2-fluoro-phenyl)-2-methanesulfonyl-2-methyl-butyric acid ethyl ester

Product 1

HCID 665779184-(4-Bromo-2-fluoro-phenyl)-2-methanesulfonyl-2-methyl-butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was synthesized according to the general procedure of Preparation 2, Step 3, for the preparation of (II) except that 4-(4-bromo-2-fluoro-phenyl)-2-methanesulfonyl-2-methyl-butyric acid ethyl ester was used instead of (+/−)-ethyl 4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoate and that lithium hydroxide was dissolve in water prior to addition to yield as a white solid: 1.96 g, (96.2%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.76 (s, 3H) 2.23 (td, 1H) 2.47 (td, J=12.59, 4.88 Hz, 1H) 2.63 (td, J=12.88, 4.68 Hz, 1H) 2.84 (td, J=12.49, 5.07 Hz, 1H) 3.11 (s, 3H) 7.10 (t, J=8.20 Hz, 1H) 7.20-7.23 (m, 1H) 7.25-7.34 (m, 1H)

Workup

  1. additionto addition
  2. customto yield as a white solid

Sources & evidence

ORD record
ord-9eb6e97766ec4c01b1f8acbb003e9999
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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