Hydrochloric Acid → HCID 19351633, compound

HRID 1636435Notes

Reaction equation

HRID 1636435 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH2:12][CH2:13][CH3:14])=[C:7](Cl)[C:6]=2[CH:16]=1.[H-].[Na+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH2:12][CH2:13][CH3:14])=[C:7]([O:27][C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 193516286-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one

Product 1

HCID 19351633HCID 19351633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one (0.5 g) with sodium hydride (0.8 g of 60% in oil) and 4-methoxyphenol (0.24 g) in dry dimethylformamide (5 ml) was stirred at room temperature overnight under nitrogen. The mixture was poured into dilute hydrochloric acid and extracted with diethyl ether. The extracts were washed with sodium hydroxide, brine, dried and evaporated under reduced pressure. The residue was triturated with light petroleum (b.p. 40-60° C.) to give 6-bromo-4-(4-methoxyphenoxy)-3-propyl-2H-1-benzopyran-2-one, m.p. 104-6° C. (compound 20).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with sodium hydroxide, brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with light petroleum (b.p. 40-60° C.)

Sources & evidence

ORD record
ord-148e3dbb622c405f93c8d457971483dd
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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