Chloroform → Benzo(B)Thiophene

HRID 358459Notes

Reaction equation

HRID 358459 reaction equation
Cl[C:2]1[S:6][CH:5]=[CH:4][C:3]=1[CH2:7]Br.[Cl-].C[N+](C(=O)CCCCCCC)(C(=O)CCCCCCC)[C:12](=O)[CH2:13][CH2:14]CCCCC.C(Cl)(Cl)Cl>O1CCCC1.[OH-].[Na+]>[S:6]1[CH:5]=[CH:4][C:3]2[CH:7]=[CH:12][CH:13]=[CH:14][C:2]1=2

Participants

6

Reactant 3

HCID 6212ChloroformHCID 109327473-(Bromomethyl)-2-chlorothiopheneHCID 14567419HCID 14567419, compound

Product 1

HCID 7221Benzo(B)Thiophene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Stir cis-6-chloro-2,3-dihydro-3-hydroxy-2-[(1', 2', 4'-triazolyl)-1'-methyl]benzo(b)thiophene (1.17 gms., 4.37 mmols), 2-chloro-3-thenylbromide (1.06 gms., 5.0 mmol) and methyl tricaprylyl ammonium chloride (0.1 gm.) in tetrahydrofuran (25 ml) and 50% sodium hydroxide (10 ml) at room temperature for one hour. Pour the reaction mixture into chloroform (500 ml.) and extract with two 500 ml. portions of water. Dry the chloroform solution over anhydrous magnesium sulfate, filter and evaporate in vacuo. Chromatograph the resultant residue on silica gel eluting with chloroform. Combine the like eluates as determined by thin layer chromatography and evaporate in vacuo to obtain cis-6-chloro-3-(2'-chloro-3'-thenyloxy)-2,3-dihydro-2-[(1", 2", 4"-triazolyl)-1"-methyl]benzo(b)thiophene, a gum.

Workup

  1. extractionextract with two 500 ml
  2. dry with materialDry the chloroform solution over anhydrous magnesium sulfate
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-5052d824b32442f4bf703e2fd74e47d6
Source dataset
uspto-grants-1984_08
Patent number
US04468404

Reaction notes

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