HCID 20728732, compound → HCID 20728731, compound

HRID 722791Notes

Reaction equation

HRID 722791 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:19]([O:21][CH3:22])=[O:20])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=2)=[CH:7][CH:8]=1.[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>CC(C)=O>[C:23]([S:25][CH2:2][C:3]1[CH:4]=[C:5]([C:19]([O:21][CH3:22])=[O:20])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=2)=[CH:7][CH:8]=1)(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 20728732HCID 20728732, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20728731HCID 20728731, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (1.59 g, 4.4 mmol) in acetone (75 mL) was added potassium thioacetate (0.60 g, 5.3 mmol), and the mixture was refluxed for 1 h. The mixture was allowed to cool to rt, filtered, and concentrated. The residual product was purified by column chromatography (hexanes/EtOAc, 9/1) to afford 4-acetylthiomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (1.21 g, 76%): 1H NMR (DMSO-d6) δ 2.39 (s, 3H), 3.60 (s, 3H), 3.88 (s, 3H), 4.23 (s, 2H), 7.42–7.44 (d, J=8.0 Hz, 1H), 7.57–7.60 (m, 3H), 7.74 (s, 1H), 7.83 (s, 1H), 7.96–7.99 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residual product was purified by column chromatography (hexanes/EtOAc, 9/1)

Sources & evidence

ORD record
ord-269fb204136d4ce596afa167356055d1
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

Loading…