Pyridine → Isobutyl 2-bromopropionate

HRID 860296Notes

Reaction equation

HRID 860296 reaction equation
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[Br:12][CH:13]([CH3:17])[C:14](Br)=[O:15]>C(OCC)C>[Br:12][CH:13]([CH3:17])[C:14]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6560IsobutanolHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 522337Isobutyl 2-bromopropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of iso-butanol and 1.0 equivalent of pyridine in dry diethyl ether was added dropwise 1.3 equivalents of 2-bromopropionyl bromide at 0° C. After stirring at room temperature for 16 hours, the reaction was diluted with diethyl ether, washed with 1N HCl, water, aqueous NaHCO3, brine and dried over magnesium sulfate or sodium sulfate. Removal of the solvents at reduced pressure gave the title compound as a clear oil.

Workup

  1. washwashed with 1N HCl, water, aqueous NaHCO3, brine
  2. dry with materialdried over magnesium sulfate or sodium sulfate
  3. customRemoval of the solvents at reduced pressure

Sources & evidence

ORD record
ord-03aaf289523447b29e17111490b66d3b
Source dataset
uspto-grants-2006_12
Patent number
US07153847B2

Reaction notes

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