Hydrogen Bromide → Methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoate

HRID 335217Notes

Reaction equation

HRID 335217 reaction equation
Br[C:2](=[CH2:12])[CH2:3][C:4]([O:10][CH3:11])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].C(#N)C.BrN1C(=[O:22])CCC1=O.[BrH:24]>ClCCl.O>[Br:24][CH2:12][C:2](=[O:22])[CH2:3][C:4]([O:10][CH3:11])([CH3:9])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 86631519Methyl 4-bromo-2-methoxy-2-methylpent-4-enoate

Product 1

HCID 86631520Methyl 5-bromo-2-methoxy-2-methyl-4-oxopentanoateYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 125 mL round-bottom flask, methyl 4-bromo-2-methoxy-2-methylpent-4-enoate (0.525 g, 2.21 mmol) was added acetonitrile (8 mL), water (2 mL) and N-bromosuccinimide (0.493 g, 2.77 mmol). A catalytic amount of 1M HBr was added (0.066 mL, 0.066 mmol). The resulting solution was agitated overnight, diluted with 50 mL of dichloromethane and washed twice with saturated sodium bicarbonate, dried and evaporated. The residue was purified by chromatography on silica gel, eluting with 10% ethyl acetate/hexane to provide the title compound (0.52 g, 92.8% yield) as clear oil.

Workup

  1. washwashed twice with saturated sodium bicarbonate
  2. customdried
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel
  5. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ac2218d76d1a48098e7a0bec87739260
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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