Hydrochloric Acid → 4-Bromo-2-(3-fluoro-4-nitro-phenoxy)-butyric acid methyl ester

HRID 1678634Notes

Reaction equation

HRID 1678634 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH:13]([CH2:18][CH2:19][Br:20])[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:17][O:16][C:14](=[O:15])[CH:13]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[CH2:18][CH2:19][Br:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 296716Methyl 2,4-dibromobutanoateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 671310624-Bromo-2-(3-fluoro-4-nitro-phenoxy)-butyric acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 5.5 g (35.0 mmol) 3-fluoro-4-nitrophenol (CAS Reg. No. 399-95-1) in 55 mL N,N-dimethylformamide, 11.8 g (45.5 mmol) methyl 2,4-dibromobutyrate (CAS Reg. No. 29547-04-4) and 6.3 g (45.5 mmol) potassium carbonate were added. After stirring for 3 h the reaction mixture was poured on ethyl acetate and 1 M aqueous hydrochloric acid and extracted. The organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (1:0 to 1:1 v/v) to afford the title compound as a light yellow oil (64%) which was pure enough to be used in the next step.

Workup

  1. extractionextracted
  2. washThe organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.)
  7. washeluting with a gradient of heptane:ethyl acetate (1:0 to 1:1 v/v)

Sources & evidence

ORD record
ord-a730647874254c33b5f12f26ffa27b27
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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