Quinoline → HCID 13563467, compound

HRID 2290175Notes

Reaction equation

HRID 2290175 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:6][CH:5]=1.N1C2C(=CC=CC=2)C=CC=1>CCOCC>[Br:1][CH2:14][CH:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)[O:15]1

Participants

5

Reactant 3

HCID 7047QuinolineHCID 24408BromineHCID 11435538HCID 11435538, compound

Product 1

HCID 13563467HCID 13563467, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

16 g (0.1 mole) of bromine are added dropwise to 17.3 g (0.1 mole) of 5-(4-chlorophenyl)-pent-1-en-5-ol in 50 ml of absolute ether at 0° C. When the addition has ended, 13 g (0.1 mole) of quinoline are added, whereupon the temperature rises to 15° C. and quinoline hydrobromide precipitates. The precipitate is filtered off with suction, the filtrate is evaporated in vacuo and the residue is heated on a waterbath for 1 hour. After cooling, the residue is taken up in ether, the mixture is washed with 15% strength hydrochloric acid and with water, dried over sodium sulphate and concentrated in vacuo and the residue is distilled under a high vacuum. 5 g (18% of theory) of 2-bromomethyl-5-(4-chlorophenyl)tetrahydrofuran of boiling point 145° C./0.13 mbar are obtained. ##STR111##

Workup

  1. additionWhen the addition
  2. customrises to 15° C.
  3. customquinoline hydrobromide precipitates
  4. filtrationThe precipitate is filtered off with suction
  5. customthe filtrate is evaporated in vacuo
  6. temperaturethe residue is heated on a waterbath for 1 hour
  7. temperatureAfter cooling
  8. washthe mixture is washed with 15% strength hydrochloric acid and with water
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated in vacuo
  11. distillationthe residue is distilled under a high vacuum

Sources & evidence

ORD record
ord-30052c59463146c9a4a7d293b80f566d
Source dataset
uspto-grants-1986_10
Patent number
US04615725

Reaction notes

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