Methyl 2,6-dibromohexanoate → Methyl 2-(acetylthio)-6-bromohexanoate
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was quenched with water
- extractionextracted with ether
- washwashed with water, brine
- dry with materialdried (MgSO4)
- customThe crude isolate
- 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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