Dimethylformamide → 3-(4-bromophenyl)-6-ethyl-7-hydroxy-4H-chromen-4-one

HRID 1296876Notes

Reaction equation

HRID 1296876 reaction equation
[CH2:1]([C:3]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:4]=1O)[CH3:2].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.P(Cl)(Cl)(Cl)(Cl)Cl.CN([CH:31]=[O:32])C>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19](=[O:21])[C:6]3[C:7](=[CH:8][C:9]([OH:10])=[C:3]([CH2:1][CH3:2])[CH:4]=3)[O:32][CH:31]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24819Phosphorus pentachlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 98339742-Ethylresorcinol

Product 1

HCID 53996383-(4-bromophenyl)-6-ethyl-7-hydroxy-4H-chromen-4-oneYield 82.3%

Procedure

This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), 4-bromophenylacetic acid (1.29 g, 6 mmol), BF3Et2O (5 ml), PCl5 (1.99, 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-ethyl-7-hydroxy-chromen-4-one as a pale pink solid (1.7 g, 82.3%); Rf 0.84 ethyl acetate.

Workup

  1. customThis compounds was synthesised in the same manner
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customre-crystallized from methanol

Sources & evidence

ORD record
ord-83709207bd964813b08925a05822fc79
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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