Bromine → HCID 19858046, compound

HRID 2073390Notes

Reaction equation

HRID 2073390 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH3:16])=[C:12]([C:17]#[N:18])[CH:11]=3.[Br:20]Br.C(=O)([O-])O.[Na+]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[Br:20][C:14]1[C:13]([CH3:16])=[C:12]([C:17]#[N:18])[CH:11]=[C:10]2[C:15]=1[C:3]1[C:2]([CH3:19])([CH3:1])[C:6](=[O:7])[O:5][C:4]=1[CH:8]=[CH:9]2

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 19858070HCID 19858070, compound

Product 1

HCID 19858046HCID 19858046, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1,2-dihydro-1,1,8-trimethyl-2-oxonaphtho[2,1-b]furan-7-carbonitrile (0.25 g), silver trifluoromethanesulphonate (0.34 g) and dichloromethane (10 ml) was stirred in the dark, while a solution of bromine (0.19 g) in dichloromethane (2 ml) was added over 10 minutes. The mixture was stirred a further 0.5 h, then treated with aqueous sodium hydrogen carbonate solution, and the resulting mixture was filtered through a pad of diatomaceous earth ("Celite" -trade mark). The organic phase was separated, dried and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography, using chloroform:pentane, 1:1 v/v, as eluant, to give 9-bromo-1,2-dihydro-1,1,8-trimethyl-2-oxonaphtho[2,1-b]furan-7-carbonitrile, m.p. 235°-237° after recrystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80°), which was brominated by the process described in the last part of Example 4.

Workup

  1. additionwas added over 10 minutes
  2. filtrationthe resulting mixture was filtered through a pad of diatomaceous earth ("Celite" -trade mark)
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5859ffb018ea43d586eb0b53b477fc28
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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