Potassium Carbonate → Ethyl 3-(2-bromophenylthio)propanoate

HRID 1523842Notes

Reaction equation

HRID 1523842 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69341Ethyl 3-chloropropionateHCID 805982-Bromobenzenethiol

Product 1

HCID 43365405Ethyl 3-(2-bromophenylthio)propanoateYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromobenzenethiol (6 g, 30 mmol), ethyl 3-chloropropanoate (13 g, 96 mmol), K2CO3 (8.8 g, 64 mmol) and acetone (150 mL) was refluxed for 15 h. The reaction mixture was filtered and the filter cake washed with acetone (50 mL). The filtrate was concentrated to dryness and subjected to FCC to give ethyl 3-(2-bromophenylthio)propanoate (7 g, 78%). MS (ESI): mass calcd. for C11H13O2S, 287.98; m/z found, 288.8 [M+H]+.

Workup

  1. temperaturewas refluxed for 15 h
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake washed with acetone (50 mL)
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c3d80b2c650e435cbc19e04aea7ca6d8
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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