Dimethyl Ether → 3-Chloro-5-hydroxybenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Cl)[CH:9]=1)[C:5]#[N:6].ClCl.C[O-].[Na+].C[O:17]C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:17])[CH:9]=1)[C:5]#[N:6]Participants
5
Procedure
The requisite phenols utilized in the condensation with 15 or 18b were prepared as depicted in SCHEME 3. Dibromofluorobenzene (20a) was treated with sodium methoxide resulting in displacement of the fluorine substituent to afford 20b. Monometallation and formylation of the resulting lithium salt with DMF afforded 21. Conversion of the formyl group into a difluoromethyl group was effected with DAST. Demethylation of the methyl ether afforded the requisite phenol 23. 3-Chloro-5-hydroxy-benzonitrile (24c) was prepared form 3,5-dichloro-benzonitrile by displacement of a chlorine substitutent with sodium methoxide and demethylation of the resulting ether to afford 24c.
Sources & evidence
- ORD record
- ord-f85c39ce454a4c55bbdea39449a43c9a
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754919B2
Reaction notes
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