4-Chlororesorcinol → HCID 58913628, compound

HRID 1296879Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:27]N(C=O)C>>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18](=[O:20])[C:7]3[C:5](=[CH:4][C:3]([OH:9])=[C:2]([Cl:1])[CH:8]=3)[O:6][CH:27]=2)=[CH:15][CH:16]=1

Participants

Reactant 4

HCID 17314-Chlororesorcinol

HCID 6228Dimethylformamide

HCID 24819Phosphorus pentachloride

HCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 58913628HCID 58913628, compound

Procedure

This compounds was synthesised in the same manner as described above. 4-Chlororesorcinol (0.87 g, 6 mmol), 4-bromophenyl acetic acid (1.29 g, 6 mmol), BF3Et2O (4 ml), PCl5 (1.9 g, 9.1 mmol), DMF (5 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 3-(4-Bromo-phenyl)-6-chloro-7-hydroxy-chromen-4-one a flakey white solid (1.2 g, 56.8%); Rf 0.81 ethyl acetate.

Workup

customThis compounds was synthesised in the same manner
customThe precipitate formed
filtrationwas filtered
customre-crystallized from methanol

Sources & evidence

ORD record: ord-c6bfa568c51c416a89e27b5634973355
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247734B2

Reaction notes

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