Bromoform → Dimethyl 2-bromo-2-methylmalonate

HRID 654612Notes

Reaction equation

HRID 654612 reaction equation
C(Br)(Br)[Br:2].[CH3:5][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:7]([O:9][CH3:10])=[O:8]>O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)(Cl)Cl>[Br:2][C:6]([CH3:5])([C:11]([O:13][CH3:14])=[O:12])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 5558BromoformHCID 69104Dimethyl methylmalonate

Product 1

HCID 12681741Dimethyl 2-bromo-2-methylmalonateYield 89.4%

Reagents, catalysts & solvents 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Bromoform (1.01 g, 0.4 mol), 1.46 g dimethyl methylmalonate, 200 mg tetra-n-butylammonium fluoride trihydrate (0.632 mmol), and 5 mL carbon tetrachloride were mixed at 24° C. for 2 h. The solution was found to contain 2.01 g (89% yield) of dimethyl α-bromo-α-methylmalonate.

Sources & evidence

ORD record
ord-4bb6ff8b07b0433d905537e877b442f6
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Reaction notes

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