3,4-Dibromothiophene → HCID 13924248, compound

HRID 2308590Notes

Reaction equation

HRID 2308590 reaction equation
[Br:1][C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](Cl)=[O:14].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[Br:1][C:2]1[C:6]([Br:7])=[CH:5][S:4][C:3]=1[C:13]([C:9]1[S:8][CH:12]=[CH:11][CH:10]=1)=[O:14]

Participants

5

Reactant 3

HCID 184523,4-DibromothiopheneHCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13924248HCID 13924248, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 30 g of 3,4-dibromothiophene and 13.5 mL of thiophene-2-carbonylchloride in 120 mL of carbon disulfide was added 16.5 g aluminum trichloride portionwise over 10 minutes. The mixture was stirred for 3 hours, poured into 900 g of ice-water and extracted with methylene chloride. The organic layer was washed with 1N NaOH (aq), water, and dried (MgSO4). Filtration and concentration of the filtrate, in vacuo, afforded an oil which crystallized upon trituration with n-chlorobutane to yield 32 g of the subject compound as an off-white solid, m.p. 105°-109° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with 1N NaOH (aq), water
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration of the filtrate
  5. customin vacuo, afforded an oil which
  6. customcrystallized upon trituration with n-chlorobutane

Sources & evidence

ORD record
ord-bdb06a9177f84bbeb7afa9b9b68f76fb
Source dataset
uspto-grants-1987_09
Patent number
US04690705

Reaction notes

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