Thiophenol → HCID 20991675, compound

HRID 2089499Notes

Reaction equation

HRID 2089499 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12].[F-].[K+]>CN(C=O)C>[CH3:9][C:10]([CH3:15])([CH2:14][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 2719323-Bromo-2,2-dimethylpropanoic acidHCID 522689Potassium Fluoride

Product 1

HCID 20991675HCID 20991675, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of thiophenol (5 g, 45 mmol) in DMF (100 mL) is added 3-bromo-2,2-dimethyl-propionic acid (CAS#2843-17-6, 3.98 g, 22 mmol), and potassium fluoride (1.56 g, 27 mmol). The reaction is heated at 120° C. overnight. The reaction is then cooled to room temperature and poured into ice water. A white precipitate is filtered and washed with ice water. The solid is then dissolved in 1M aqueous NaOH and is washed with dichloromethane. The aqueous solution is acidified with 1M HCl and the resulting precipitate is collected to provide 2,2-dimethyl-3-phenylsulfanyl-propionic acid; 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (s, 6 H), 2.72 (br. s., 1 H), 3.19 (s, 2 H), 7.09-7.21 (m, 1 H), 7.21-7.32 (m, 2 H), 7.40 (d, J=7.8 Hz, 2 H).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. filtrationA white precipitate is filtered
  3. washwashed with ice water
  4. dissolutionThe solid is then dissolved in 1M aqueous NaOH
  5. washis washed with dichloromethane
  6. customthe resulting precipitate is collected

Sources & evidence

ORD record
ord-5783a0bb60194a4cb6061b15188c01c4
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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