Potassium tert-butoxide → 1-(3-Fluoro-4-nitro-phenoxy)-cyclopropanecarboxylic acid methyl ester

HRID 1161349Notes

Reaction equation

HRID 1161349 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([F:18])[CH:10]=1)[CH2:5][CH2:6]Br.CC(C)([O-])C.[K+]>O1CCCC1>[CH3:1][O:2][C:3]([C:4]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([F:18])[CH:10]=2)[CH2:6][CH2:5]1)=[O:19]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 671310624-Bromo-2-(3-fluoro-4-nitro-phenoxy)-butyric acid methyl ester

Product 1

HCID 671310221-(3-Fluoro-4-nitro-phenoxy)-cyclopropanecarboxylic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 7.5 g (22.3 mmol) 4-bromo-2-(3-fluoro-4-nitro-phenoxy)-butyric acid methyl ester in 100 mL tetrahydrofuran was cooled to −15° C. and 2.63 g (23.4 mmol) potassium tert-butoxide were added. The cooling bath was removed and the reaction was stirred for 5 h at room temperature. The dark solution was poured 200 mL ethyl acetate and 200 mL aqueous hydrochloric acid, extracted and the phases were separated. The organic layer was washed with brine and the aqueous layers extracted with ethyl acetate. The combined organic layers were 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 (100:30 to 70:30 v/v) to afford the title compound as a light yellow oil (79%).

Workup

  1. customThe cooling bath was removed
  2. additionThe dark solution was poured 200 mL ethyl acetate and 200 mL aqueous hydrochloric acid
  3. extractionextracted
  4. customthe phases were separated
  5. washThe organic layer was washed with brine
  6. extractionthe aqueous layers extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.)
  11. washeluting with a gradient of heptane:ethyl acetate (100:30 to 70:30 v/v)

Sources & evidence

ORD record
ord-ce15999bdbf54da2a16c242fc63a3b77
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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