2-Fluoro-4-(hydroxymethyl)benzonitrile → 2-Fluoro-4-formylbenzonitrile

HRID 1348901Notes

Reaction equation

HRID 1348901 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>O1CCOCC1.O=[Mn]=O>[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 112173392-Fluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of Example 52B (1.23 g, 8.17 mmol) in 1,4-dioxane (30 mL) was treated with MnO2, heated to 100° C. for 1 hour, and cooled to room temperature. The cooled solution was filtered through diatomaceous earth (Celite®) on a fritted funnel rinsing with 1:1 dichloromethane/methanol (200 mL). The filtrate was concentrated and the concentrate was purified by flash column chromatography on silica gel with a solvent gradient of 19:1 to 4:1 hexanes/ethyl acetate to provide the desired product. MS (APCI) m/z 149 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 10.06 (s, 1H), 7.88-7.71 (m, 3H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe cooled solution was filtered through diatomaceous earth (Celite®) on a fritted funnel
  3. washrinsing with 1:1 dichloromethane/methanol (200 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe concentrate was purified by flash column chromatography on silica gel with a solvent gradient of 19:1 to 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-3b911b03005a4785bdf37241dddc9b28
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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