Nitrogen → Methyl 4-bromo-3-oxopentanoate

HRID 892163Notes

Reaction equation

HRID 892163 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Br:10]Br.N#N>C(Cl)(Cl)(Cl)Cl>[Br:10][CH:8]([CH3:9])[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24408BromineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 9815681Methyl 4-bromo-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a cooled (0° C.) solution of methyl 3-oxopentanoate (9.62 mL, 76.8 mmoles, Acros) in carbon tetrachloride (60 mL) is added dropwise over a period of 45 minutes a solution of bromine (3.96 mL, 76.8 mmoles) in carbon tetrachloride (10 mL). After 30 minutes, let stir at room temperature for one hour. Bubbled N2 through reaction mixture for twenty minutes. Concentrated to yield the title compound as a brown oil. MS (EI) 208, 210 (M)+, Br pattern.

Workup

  1. concentrationConcentrated

Sources & evidence

ORD record
ord-cbd5817360c74a62bff25024456bf2dc
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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