Cyclohexyl bromide → 3-Methyl-1-benzothiophene-7-ol

HRID 1380078Notes

Reaction equation

HRID 1380078 reaction equation
C1(Br)CCCCC1.Cl[C:9]1[C:14]2[S:15][CH:16]=[C:17]([CH3:18])[C:13]=2[CH:12]=[CH:11][CH:10]=1.[Mg].C1C[O:23]CC1>>[OH:23][C:9]1[C:14]2[S:15][CH:16]=[C:17]([CH3:18])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 7960Cyclohexyl bromideHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 202421187-Chloro-3-methyl-1-benzothiophene

Product 1

HCID 153248073-Methyl-1-benzothiophene-7-ol

Procedure

Cyclohexyl bromide (32.6 g.) and 7-chloro-3-methylbenzo[b]thiophene (18.3 g.) in THF (400 ml) is added to a suspension of magnesium turnings (7.3 g.) in THF. The mixture is stirred for two hours and heated on a steam bath for two hours. The reaction is cooled and oxygen is bubbled in slowly for two hours. The mixture is stirred for 18 hours at room temperature and extracted with chloroform. The organic extract is extracted with 5% sodium hydroxide. The aqueous extract is acidified with concentrated hydrochloric acid and extracted with ethyl ether. The ether extract is dried (MgSO4) and concentrated to a solid.

Workup

  1. temperatureheated on a steam bath for two hours
  2. temperatureThe reaction is cooled
  3. customoxygen is bubbled in slowly for two hours
  4. stirringThe mixture is stirred for 18 hours at room temperature
  5. extractionextracted with chloroform
  6. extractionThe organic extract
  7. extractionis extracted with 5% sodium hydroxide
  8. extractionThe aqueous extract
  9. extractionextracted with ethyl ether
  10. extractionThe ether extract
  11. dry with materialis dried (MgSO4)
  12. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-21ec5330ac1945778ad9edafb0969c2b
Source dataset
uspto-grants-1986_04
Patent number
US04579865

Reaction notes

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