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

HRID 911895Notes

Reaction equation

HRID 911895 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-7989e2e5658b402080d34d9c8167c9d3
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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