Quinoline → 2-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran

HRID 986384Notes

Reaction equation

HRID 986384 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([OH:17])([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])=[CH:6][CH:5]=1.N1C2C(=CC=CC=2)C=CC=1>C(Cl)(Cl)Cl>[Br:1][CH2:15][CH:14]1[CH2:13][CH2:12][C:11]([C:10]([CH3:19])([CH3:18])[CH2:9][O:8][C:7]2[CH:20]=[CH:21][C:4]([Cl:3])=[CH:5][CH:6]=2)([CH3:16])[O:17]1

Participants

5

Reactant 3

HCID 7047QuinolineHCID 24408BromineHCID 135634657-(4-Chlorophenoxy)-5-hydroxy-5,6,6-trimethyl-hept-1-ene

Product 1

HCID 135634662-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuranYield 90.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

16 g (0.1 mole) of bromine are added dropwise to 28.2 g (0.1 mole) of 7-(4-chlorophenoxy)-5-hydroxy-5,6,6-trimethyl-hept-1-ene in 200 ml of absolute chloroform at room temperature, with stirring, followed by 13 g (0.1 mole) of quinoline, at -10° C. with cooling. The reaction mixture is stirred at room temperature for a further 2 hours and concentrated in vacuo, the residue is taken up in ether, the mixture is filtered and concentrated again in vacuo and the residue is stirred at 95° C. on a water-bath for 1 hour. The resulting mixture is taken up in ether and filtered and the filtrate is washed with 15% strength hydrochloric acid and then with water, dried over sodium sulphate and freed from the solvent in vacuo. 32.7 g (90% of theory) of 2-bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran are obtained as an oil, which can be used in the next stage without further purification. ##STR142##

Workup

  1. temperaturewith cooling
  2. stirringThe reaction mixture is stirred at room temperature for a further 2 hours
  3. concentrationconcentrated in vacuo
  4. filtrationthe mixture is filtered
  5. concentrationconcentrated again in vacuo
  6. stirringthe residue is stirred at 95° C. on a water-bath for 1 hour
  7. filtrationfiltered
  8. washthe filtrate is washed with 15% strength hydrochloric acid
  9. dry with materialwith water, dried over sodium sulphate

Sources & evidence

ORD record
ord-abbff69ade774437a3577f9313e6587e
Source dataset
uspto-grants-1987_12
Patent number
US04713379

Reaction notes

Loading…