3-Bromopropionic acid → 3-(4-Bromothiophenoxy)propionic acid

HRID 617693Notes

Reaction equation

HRID 617693 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][C:14]([OH:16])=[O:15]>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 115533-Bromopropionic acidHCID 14798Sodium HydroxideHCID 660494-Bromothiophenol

Product 1

HCID 167762423-(4-Bromothiophenoxy)propionic acidYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

8.5 g (0.211 mol) of sodium hydroxide was added to 45 mL of water, 20.0 g (0.106 mol) of 4-bromothiophenol (purchased from Aldrich Chemical Company) was then added and the mixture was cooled to about 0° C. 18.0 g (0.116 mol) of 3-bromopropionic acid (purchased from Aldrich Chemical Company) was added in portions while keeping the temperature below 5° C. The mixture was warmed to room temperature, stirred for 1 h under nitrogen, and was then washed with diethyl ether (3×100 mL). The aqueous layer was acidified with 1N HCl, and then filtered to yield 27.95 g of the title compound of Step A as a solid melting at 101-103° C. 1H NMR (CDCl3): δ2.66 (t,2H), 3.14 (t,2H), 7.2 (m,2H), 7.4 (m,2H).

Workup

  1. additionwas then added
  2. customthe temperature below 5° C
  3. temperatureThe mixture was warmed to room temperature
  4. washwas then washed with diethyl ether (3×100 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fb06d2ea53cb4146948e158ab0d0ac60
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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