Water → Methyl 4-bromo-2-nitrophenylacetate

HRID 1618486Notes

Reaction equation

HRID 1618486 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C(OC)=O)[C:9]([O:11][CH3:12])=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[Li+].[Cl-].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Product 1

HCID 15740598Methyl 4-bromo-2-nitrophenylacetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Prepared according to procedure H using dimethyl 2-(4-bromo-2-nitrophenyl)-malonate in DMSO (40 mL), LiCl (1.16 g, 27.4 mmol) and water (0.25 mL, 13.88 mmol) and heating at 100° C. for 15 h. After purification methyl 2-(4-bromo-2-nitrophenyl)acetate was obtained as an orange oil. Mass Spectrum (ESI) m/e=274 [(M+1) (79Br)] and 276 [(M+1) (81Br)].

Workup

  1. customPrepared
  2. customAfter purification methyl 2-(4-bromo-2-nitrophenyl)acetate
  3. customwas obtained as an orange oil

Sources & evidence

ORD record
ord-9cb7fbceb0764557924f0cb8539600e3
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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