Bromobenzene → HCID 12876530, compound

HRID 1395656Notes

Reaction equation

HRID 1395656 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li].Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[C:19]([CH:21]1[CH:29]2[N:24]([CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:23][CH2:22]1)=O)C>O.CCOCC>[C:1]1([C:19]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:21]2[CH:29]3[N:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:23][CH2:22]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

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

Product 1

HCID 12876530HCID 12876530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a phenyl lithium solution prepared by dissolving 0.51 g. of metallic lithium and 6.32 g. of bromobenzene in 50 ml. of absolute ether, was dropwise added a solution of 2.40 g. of 1-ethoxycarbonylindolizidine in 20 ml. of absolute ether under ice cooling. After refluxing for about 10 mins., water was dropwise added thereto, followed by extraction with ether. The ethereal layer was further extracted with dil. hydrochloric acid. The aqueous layer was rendered alkaline with an aq. sodium hydroxide 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 light yellow viscous substance was obtained.

Workup

  1. dissolutionby dissolving 0.51 g
  2. temperatureAfter refluxing for about 10 mins
  3. extractionfollowed by extraction with ether
  4. extractionThe ethereal layer was further extracted with dil. hydrochloric acid
  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 light yellow viscous substance was obtained

Sources & evidence

ORD record
ord-a3dc864c84054385b58ff0743a490607
Source dataset
uspto-grants-1980_05
Patent number
US04205074

Reaction notes

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