Bromobenzene → HCID 70595205, compound

HRID 1395660Notes

Reaction equation

HRID 1395660 reaction equation
C(O[C:4]([CH:6]1[CH:14]2[N:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)=[O:5])C.[C:15]1([Li])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li].Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.CCOCC>[C:15]1([C:4]([CH:6]2[CH:14]3[N:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)[CH2:8][CH2:7]2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[OH:5])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 3028194LithiumHCID 10932403HCID 10932403, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 70595205HCID 70595205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.40 g. of 1-ethoxycarbonylindolizidine in 20 ml. of dry ether was dropwise added to a solution of phenyl lithium prepared from 0.51 g. of metal lithium, 6.32 g. of bromobenzene and 50 ml. of dryether under ice cooling. After refluxing for about 10 mins., water was dropwise added to the reaction mixture. The mixture was extracted with ether. The ethereal layer was extracted with a diluted hydrochloric acid solution and the aqueous layer was adjusted to alkaline with a causting soda solution and then extracted with ether. The ethereal layer was washed with water and dried. After removing the solvent by distillation, 3.58 g. of yellowish viscous substance was obtained. This substance was crystallized. By recrystallization from isopropyl ether, colorless needles with a melting point of 120°-121° C. was obtained.

Workup

  1. customprepared from 0.51 g
  2. temperatureAfter refluxing for about 10 mins
  3. extractionThe mixture was extracted with ether
  4. extractionThe ethereal layer was extracted with a diluted hydrochloric acid solution
  5. extractionextracted with ether
  6. washThe ethereal layer was washed with water
  7. customdried
  8. customAfter removing the solvent
  9. distillationby distillation, 3.58 g
  10. customof yellowish viscous substance was obtained
  11. customThis substance was crystallized
  12. customBy recrystallization from isopropyl ether, colorless needles with a melting point of 120°-121° C.
  13. customwas obtained

Sources & evidence

ORD record
ord-9314066575864df3bdad57e680847abb
Source dataset
uspto-grants-1980_05
Patent number
US04205074

Reaction notes

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