Formate → 3-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one

HRID 1479176Notes

Reaction equation

HRID 1479176 reaction equation
C1(C=CC=C(O)C=1)O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](Cl)=[O:18])=[CH:12][CH:11]=1.BrC1C=CC(C[C:28]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:31]=2O)=[O:29])=CC=1.C([O-])=O>>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:28](=[O:29])[C:30]3[C:31](=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=3)[O:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 283FormateHCID 5054ResorcinolHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 20634662-(4-bromophenyl)-1-(2,4-dihydroxyphenyl)ethanone

Product 1

HCID 53983673-(4-bromophenyl)-7-hydroxy-4H-chromen-4-one

Procedure

Resorcinol is reacted with 2-(4-bromophenyl)acetyl chloride forming the product 2-(4-bromophenyl)-1-(2,4-dihydroxyphenyl)ethanone. Such reactions are described in Chemistry of Heterocyclic Compounds (NY, N.Y., USA) 1977 Vol., 13, p. 948-953. The product is reacted with triethylorth formate to form 3-(4-bromophenyl)-7-hydroxy-chromen-4-one which can be reacted with methane sulfonyl chloride and a base to form [3-(4-bromophenyl)-4-oxo-chromen-7-yl] methanesulfonate.

Sources & evidence

ORD record
ord-eb298c12ad334cf1935502297d6280af
Source dataset
uspto-grants-2016_08
Patent number
US09408826B2

Reaction notes

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