Benzoic acid, 4-fluoro-, ethyl ester → HCID 58551422, compound

HRID 1908128Notes

Reaction equation

HRID 1908128 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13]([S:16][Na])([CH3:15])[CH3:14]>CN(C=O)C.C(OCC)(=O)C>[CH:13]([S:16][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 178460994HCID 178460994, compound

Product 1

HCID 58551422HCID 58551422, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (390 mg, 2.32 mmol) and isopropylsulfanylsodium (273 mg, 2.78 mmol) in DMF (2.5 mL) was heated at 80° C. for 36 h. The reaction mixture was diluted with ethyl acetate before being washed with 1N NaOH and then brine. The organic layer was dried over sodium sulfate and evaporated. The residue was purified by column chromatography eluting with 50-100% ethyl acetate in hexanes to give ethyl 4-isopropylsulfanylbenzoate (350 mg).

Workup

  1. washbefore being washed with 1N NaOH
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography
  5. washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-87d0add18a60456b845bc34a38f53eca
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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