N-Methylformanilide → 3,5-Difluorobenzaldehyde

HRID 2295330Notes

Reaction equation

HRID 2295330 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[C:6]([F:8])[CH:7]=1.CN([CH:19]=[O:20])C1C=CC=CC=1>C(OCC)C.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH:19]=[O:20]

Participants

5

Reactant 2

HCID 66737N-MethylformanilideHCID 178505930HCID 178505930, compound2×

Product 1

HCID 5881603,5-Difluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 3,5-difluorobenzaledehyde used as a starting compound can be prepared as follows: 3,5-difluorophenylmagnesiumbromide can be prepared as described by A. Roe and W. F. Little: J.Org.Chem. 20 (1955) 1577. A solution of 3,5-difluorophenylmagnesiumbromide in diethylether is added dropwise to a solution of N-methylformanilide in tetrahydrofuran. By working up this reaction mixture, 3,5-difluorobenzaldehyde is obtained. b55 =86°-88° C.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-d53c732bdfb34d8180e803f26615771d
Source dataset
uspto-grants-1984_01
Patent number
US04424229

Reaction notes

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