Pentane → HCID 20144461, compound

HRID 649016Notes

Reaction equation

HRID 649016 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]([Br:24])(Br)Br.[CH:25]([C:27]1[C:28]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=2[S:30][CH:31]=1)=O.CCCCC>ClCCl.[Zn]>[Br:20][C:21]([Br:24])=[CH:25][C:27]1[C:28]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=2[S:30][CH:31]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20144489HCID 20144489, compound

Product 1

HCID 20144461HCID 20144461, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent3×

Procedure

1.04 g of Zn dust and 4.17 g of triphenylphosphine are taken up in dichloromethane and 5.27 of tetrabromomethane dissolved in dichloromethane added dropwise under inert gas and with cooling. Following stirring for 24 hours at room temperature 1.4 g of 3-formyl-7-methylbenzo[b]thiophene dissolved in dichloromethane are added dropwise with ice-cooling and stirring continued overnight at room temperature. Pentane is added and the precipitated Ph3PO filtered off. Evaporation of the filtrate under vacuum yields a residue which is chromatographed over silica gel to yield the title compound, M.p.=75°-78°.

Workup

  1. additionadded dropwise under inert gas
  2. temperaturewith cooling
  3. additionare added dropwise with ice-
  4. temperaturecooling
  5. filtrationthe precipitated Ph3PO filtered off
  6. customEvaporation of the filtrate under vacuum
  7. customyields a residue which
  8. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-167ed6e2d1dd40bda86a8b5bcc49e346
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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