3-Bromopropionic acid → 3-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

HRID 1602767Notes

Reaction equation

HRID 1602767 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[SH:11].Br[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[S:11][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 115533-Bromopropionic acidHCID 14798Sodium HydroxideHCID 776152,5-Xylenethiol

Product 1

HCID 167883143-(2,5-Dimethyl-phenylsulfanyl)-propionic acidYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

43.4 g (1.086 mol) of sodium hydroxide was added to 230 mL of water, 75.0 g (0.543 mol) of 2,5-dimethylthiophenol (purchased from Aldrich Chemical Company) was then added and the mixture was cooled to about 10° C. 91.30 g (0.597 mol) of 3-bromopropionic acid (purchased from Aldrich Chemical Company) was added in portions keeping the temperature below 25° C. The mixture was warmed to room temperature, stirred for 2 hr under nitrogen, and was then washed with diethyl ether (3×500 mL). The aqueous layer was acidified with 1N HCl and filtered to yield 112.79 g of the title compound of Step A as a solid melting at 97-98° C. 1H NMR (CDCl3): δ2.3 (s,3H), 2.34 (s,3H), 2.68 (t,2H), 3.1 (t,2H), 6.9 (d,1H), 7.06-7.14 (m,2H).

Workup

  1. additionwas then added
  2. customthe temperature below 25° C
  3. temperatureThe mixture was warmed to room temperature
  4. washwas then washed with diethyl ether (3×500 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4cd5621e344748c7b95bf7719459a492
Source dataset
uspto-grants-1999_11
Patent number
US05985799

Reaction notes

Loading…