Methyl 2,6-dibromohexanoate → Methyl 2-(acetylthio)-6-bromohexanoate

HRID 520424Notes

Reaction equation

HRID 520424 reaction equation
[C:1](=[S:4])([O-:3])[CH3:2].[K+].Br[CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][Br:16])[C:8]([O:10][CH3:11])=[O:9]>CS(C)=O>[C:1]([S:4][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][Br:16])[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5122323Methyl 2,6-dibromohexanoateHCID 23670855Potassium ethanethioate

Product 1

HCID 86690127Methyl 2-(acetylthio)-6-bromohexanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Neat potassium ethanethioate (571 mg, 5 mmol) was added to a solution of methyl 2,6-dibromohexanoate (1440 mg, 5 mmol) in DMSO (5 mL) and the mixture was stirred at rt overnight. The reaction was quenched with water and extracted with ether, washed with water, brine and dried (MgSO4). The crude isolate was purified by silica gel FCC (DCM) to afford methyl 2-(acetylthio)-6-bromohexanoate as a clear oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customThe crude isolate
  6. customwas purified by silica gel FCC (DCM)

Sources & evidence

ORD record
ord-003d7b7362c84dccbe7552a9d804c524
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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