Hydrochloric Acid → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

HRID 1618485Notes

Reaction equation

HRID 1618485 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:14][CH3:15])(=[O:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10].[Br:16][C:17]1[CH:22]=[CH:21][C:20](F)=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1.Cl>CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:8]([C:7]([O:14][CH3:15])=[O:13])[C:9]([O:11][CH3:12])=[O:10])=[C:19]([N+:24]([O-:26])=[O:25])[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to procedure G using potassium carbonate (94.23 g, 681.8 mmol), dimethyl malonate (39.1 mL, 340.9 mmol) and 4-bromo-1-fluoro-2-nitrobenzene (28 mL, 227.27 mmol) in DMF (227 mL). After pouring over 200 mL of 2N aqueous HCl the precipitate was collected by filtration and washed with water (4 L) to give dimethyl 2-(4-bromo-2-nitrophenyl)malonate. Mass Spectrum (ESI) m/e=332 [(M+1) (79Br)] and 334 [(M+1) (81Br)].

Workup

  1. customPrepared
  2. filtrationwas collected by filtration
  3. washwashed with water (4 L)

Sources & evidence

ORD record
ord-f0fdedef29004b2aaed506c3305bf376
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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