Cesium carbonate → Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270105Notes

Reaction equation

HRID 270105 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:26][C@@H:27]2[CH2:29][O:28]2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 71655301Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoateYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-fluoro-2-hydroxybenzoate (456.3 mg, 1.76 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (300 mg, 1.76 mmol) and Cs2CO3 (687.4 mg, 2.11 mmol) in DMF (4.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O, organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was opurified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit) to give the subtitled compound (385 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O, organic layer
  2. dry with materialwas dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3296f6dec6e49f29eb1e5ed177a23ad
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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