Cornforth reagent → 2-(4-Fluorophenylthio)-6-fluorobenzaldehyde

HRID 1974757Notes

Reaction equation

HRID 1974757 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][C:30]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:31]=2[CH2:32][OH:33])=[CH:25][CH:24]=1>C(Cl)Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([S:29][C:30]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:31]=2[CH:32]=[O:33])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 545494552-(4-Fluorophenylthio)-6-fluorobenzyl alcohol

Product 1

HCID 191022122-(4-Fluorophenylthio)-6-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium dichromate (8.34 g, 22.2 mmol) is suspended in 30 ml of methylene chloride. A solution of 2-(4-fluorophenylthio)-6-fluorobenzyl alcohol (3.73 g, 14.8 mmol) in 10 ml of methylene chloride is then added dropwise to the suspension. The reaction mixture is then stirred overnight. The reaction mixture is filtered through diatomaceous earth (Celite®) and then through silica gel to afford the subtitle compound. m.p. 94°-97° C.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth (Celite®)

Sources & evidence

ORD record
ord-5e61816a032a49d2a34f30b7e08e5517
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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