2-Bromopropane → HCID 57830115, compound

HRID 1095405Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.Br[CH:22]([CH3:24])[CH3:23]>>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:6](=[O:20])[C:5]3[C:10](=[CH:11][C:2]([O:1][CH:22]([CH3:24])[CH3:23])=[CH:3][CH:4]=3)[O:9][CH:8]=2)=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 63582-Bromopropane

HCID 5280378Formononetin

Product 1

HCID 57830115HCID 57830115, compound

Procedure

As described in Scheme 1, treatment of 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one (1) with 2-bromopropane gives 3-(4-methoxyphenyl)-7-isopropoxy-4H-chromen-4-one (2) which is then reacted with NH2OH to give 5-isopropoxy-2-(4-(4-methoxyphenyl)isoxazol-5-yl)phenol (3) in a good overall yield. Reaction of 3 with polyethylenedibromide affords monobromoisoxazoles 4 which are respectively treated with substituted amines to afford the respective aminoalkoxy substituted 4,5-diphenylisokazoles 5.

Sources & evidence

ORD record: ord-02be5b0a1f92439d80e87161176cf559
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138184B2

Reaction notes

Loading…