Bromoform → Dimethyl 2-bromo-2-methylmalonate

HRID 654611

Reaction equation

HRID 654611 reaction equation
[Br:1]C(Br)(Br)Br.[CH3:6][CH:7]([C:12]([O:14][CH3:15])=[O:13])[C:8]([O:10][CH3:11])=[O:9].C(Br)(Br)Br>O1CCCC1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:7]([CH3:6])([C:12]([O:14][CH3:15])=[O:13])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 5558BromoformHCID 11205Carbon tetrabromideHCID 69104Dimethyl methylmalonate

Product 1

HCID 12681741Dimethyl 2-bromo-2-methylmalonateYield 87.5%

Reagents, catalysts & solvents 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.25 g tetrabromomethane (10 mmol), 1.46 g dimethyl methylmalonate (10 mmol), and 100 mg tetra-n-butylammonium fluoride trihydrate (0.316 mmol) in 5 mL tetrahydrofuran (THF) was stirred for 10 min at 24° C. Gas chromatographic analysis of the resulting mixture showed that it contained 87% yield of both dimethyl α-bromo-α-methylmalonate (1.97 g) and bromoform (2.2 g).

Sources & evidence

ORD record
ord-2a12a76e248e475dbe388e32650d1b85
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Linked notes

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