1,3-Dibromopropane → HCID 54222889, compound

HRID 1200049Notes

Reaction equation

HRID 1200049 reaction equation
[S:1]1[C:5]([CH:6]=[CH:7][C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]1=2.O1CCCC1.C1([Li])C=CC=CC=1.[Br:29][CH2:30][CH2:31][CH2:32]Br>C1CCCCC1>[S:1]1[C:5]([CH:6]=[CH:7][C:8]2[S:9][C:10]([CH2:32][CH2:31][CH2:30][Br:29])=[CH:11][CH:12]=2)=[CH:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]1=2

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 8028TetrahydrofuranHCID 53995850HCID 53995850, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 54222889HCID 54222889, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a stirred, chilled (-65° C.) solution of 2-[2-(benzo[b]thiophen-2-yl)-ethenyl]thiophene (8.1 g) and tetrahydrofuran (100 ml) was added over 15 mins phenyl lithium (18 ml of a 2.0M solution in cyclohexane). The mixture was stirred for 1 hr, and 1,3-dibromopropane (40.5 g) was added. The solution was allowed to warm to room temperature, and was refluxed overnight. The reaction mixture was quenched with methanol (30 ml) and water (100 ml). The organic phase was evaporated in vacuo, and the residue was extracted with dichloromethane. The combined, dried over anhydrous sodium sulfate organic phase was concentrated. The residue was purified by high pressure liquid chromatography (silica gel, eluted with 7:1 hexane: dichloromethane). The appropriate fractions were combined and evaporated to yield 2.15 g (18%) of product, mp 109°-111° C.

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction mixture was quenched with methanol (30 ml) and water (100 ml)
  3. customThe organic phase was evaporated in vacuo
  4. extractionthe residue was extracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate organic phase
  6. concentrationwas concentrated
  7. customThe residue was purified by high pressure liquid chromatography (silica gel, eluted with 7:1 hexane: dichloromethane)
  8. customevaporated

Sources & evidence

ORD record
ord-fcb655dcfd594fe799d7a0885d772611
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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