Hydrochloric Acid → Methyl 4-bromo-2-nitrophenylacetate

HRID 250256Notes

Reaction equation

HRID 250256 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Cl.[C:16]([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2715514-Bromo-2-nitrophenylacetic Acid

Product 1

HCID 15740598Methyl 4-bromo-2-nitrophenylacetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of (4-bromo-2-nitro-phenyl)-acetic acid (5.00 g, 19.2 mmol) in methanol (100 mL) is treated with conc. HCl (1.0 mL). The mixture is stirred at 85° C. for 16 hours and cooled to room temperature. The mixture is neutralized with aqueous Na2CO3 and concentrated under reduced pressure. The residue is extracted with ethyl acetate (50 mL×2), and the combined organic layers are dried over sodium sulfate and concentrated under reduced pressure to provide the title compound (5.27 g, 100%) as a brown solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue is extracted with ethyl acetate (50 mL×2)
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39c68c4774554e8bb89b8a0df36ed1e9
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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