tert-Butyl methyl ether → 2-Fluoro-4-formylbenzonitrile

HRID 2231807Notes

Reaction equation

HRID 2231807 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]#[N:11])[CH2:5][OH:6].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(OC)(C)(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]#[N:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrileHCID 178418287HCID 178418287, compound

Product 1

HCID 112173392-Fluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 22 g of 3-fluoro-4-cyanobenzyl alcohol in 50 ml of methylene chloride is added, with stirring, to 48 g of PCC in 150 ml of methylene chloride. After one hour 300 ml of methyl tert.-butyl ether are added to the reaction mixture and the latter is filtered, with the addition of Celite. Removing the solvent and recrystallising the residue from aqueous ethanol gives 3-fluoro-4-cyanobenzaldehyde, m.p. 83°-85°, IR (cm-1): 3089, 2880, 2239, 1699, 1571, 1499, 1486, 1428, 1392, 1299, 1251, 1140, 1111, 971, 900, 839, 753; 1H-NMR (200 MHz): (ppm): 7.7-8.0 (m, 3H, aromatic), 10.1 (s, 1H, CHO).

Workup

  1. filtrationthe latter is filtered, with the addition of Celite
  2. customRemoving the solvent
  3. customrecrystallising the residue from aqueous ethanol

Sources & evidence

ORD record
ord-b1d39826fe0c4d0eb785a6dcdaebc1b5
Source dataset
uspto-grants-1988_11
Patent number
US04784471

Reaction notes

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