Ethanol → Ethyl 2-fluoro-5-iodobenzoate

HRID 528853Notes

Reaction equation

HRID 528853 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17][CH2:18]O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27789252-Fluoro-5-iodobenzoic acid

Product 1

HCID 24820419Ethyl 2-fluoro-5-iodobenzoateYield 84%

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluoro-5-iodobenzoic acid (Oakwood, 0.99 g, 3.72 mmol) in EtOH (7.4 mL) was added H2SO4 (198 μL, 3.72 mmol). The resulting reaction mixture was stirred at 100° C. overnight and then concentrated in vacuo. The crude oil was purified using flash column chromatography (gradient from 0% to 10% EtOAc/hexanes) to give the title compound (916 mg, 84%) as a colorless oil. 1H NMR (CDCl3) δ 8.24 (dd, J=6.8, 2.4 Hz, 1H), 7.81 (ddd, J=8.8, 4.5, 2.4 Hz, 1H), 6.93 (dd, J=10.3, 8.6 Hz, 1H), 4.41 (q, J=7.0 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe crude oil was purified

Sources & evidence

ORD record
ord-8ef72e3e00ca479aa2c73b67d33c24d4
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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