Pyridine → HCID 20522455, compound

HRID 223121Notes

Reaction equation

HRID 223121 reaction equation
[Br:1]Br.[CH:3]([CH:6]1[C:14]2[C:9](=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=2)[C:8]([CH3:17])([CH3:16])[CH:7]1[CH3:18])([CH3:5])[CH3:4].N1C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:17])([CH3:16])[CH:7]([CH3:18])[CH:6]2[CH:3]([CH3:5])[CH3:4])=[CH:10][C:11]=1[CH3:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 30178881,1,2,6-Tetramethyl-3-(propan-2-yl)-2,3-dihydro-1H-indene

Product 1

HCID 20522455HCID 20522455, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

40 ml Bromine is added at 10° C. to a solution of 100 g 1-isopropyl-2,3,3,5-tetramethyl indan (obtained according to Example I or II) and 1 ml pyridine in 50 ml carbon tetrachloride. Then the reaction mixture is stirred during one hour and poured out into an aqueous solution of approximately 25 g sodium thiosulphate. The organic layer is separated, washed with 25% sodium hydroxide and evaporated. The residue is distilled under diminished pressure yielding 105 g 6-bromo-1-isopropyl-2,3,3,5-tetramethyl indan. B.p. 145°-150° C./1 mm Hg. 25 g Dimethyl formamide is added to a solution of 1-isopropyl-2,3,3,5-tetramethyl-6-indanyl magnesium bromide, prepared from 9 g magnesium and 100 g of the 6-bromo indan obtained above. The reaction mixture is then heated to reflux during 30 min., poured out into a mixture of ice and diluted sulphuric acid and extracted with ether. The solution in ether is washed neutral, dried and evaporated. The residue is distilled under diminished pressure yielding 30 g 6-formyl-1-isopropyl-2,3,3,5-tetramethyl indan. B.p. 135° C./1 mm Hg.

Workup

  1. customThe organic layer is separated
  2. washwashed with 25% sodium hydroxide
  3. customevaporated
  4. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-0e04c0a418a04d14a3d95650a26035a6
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Reaction notes

Loading…