Hexane → HCID 178445604, compound

HRID 1982125Notes

Reaction equation

HRID 1982125 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C@H:29]1[CH2:34][CH2:33][C@H:32]([CH:35]=O)[CH2:31][CH2:30]1)[CH2:26][CH2:27][CH3:28].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178445650HCID 178445650, compound

Product 1

HCID 178445604HCID 178445604, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution, cooled to -20° C., of 398 g of tetrabromomethane in 1 l of methylene chloride was treated dropwise under nitrogen gasification within 30 minutes with a solution of 629.6 g of triphenylphosphine in 1 l of methylene chloride. The mixture was subsequently stirred at -10° C. for a further 30 minutes, then treated dropwise within 30 minutes with a solution of 101 g of trans-4-butylcyclohexanecarboxaldehyde in 500 ml of methylene chloride and stirred at -5° C. for a further 2 hours. The mixture was poured into 4 l of hexane, the resulting mixture was stirred at -20° C. for 1 hour and then the precipitate was filtered off under suction and rinsed well with 1 l of cold (-20° C.) hexane. The filtrate was concentrated to a volume of about 1 l on a rotary evaporator, diluted with 2 l of hexane, again concentrated to a volume of about 1 l and stirred at -20° C. for a further 30 minutes. The precipitate was filtered off under suction and rinsed well with 700 ml of cold (-20° C.) hexane. The filtrate was freed from solvent on a rotary evaporator and the resulting yellow oil (195 g) was filtered chromatographically on silica gel with about 3 l of hexane. The eluate was evaporated up to constant weight on a rotary evaporator, there being obtained 171.3 g (88.1%) of trans-1-(2,2-dibromovinyl)-4-butylcyclohexane as a colourless liquid; Rf-value (hexane) 0.55.

Workup

  1. stirringstirred at -5° C. for a further 2 hours
  2. stirringthe resulting mixture was stirred at -20° C. for 1 hour
  3. filtrationthe precipitate was filtered off under suction
  4. washrinsed well with 1 l of cold (-20° C.) hexane
  5. concentrationThe filtrate was concentrated to a volume of about 1 l on a rotary evaporator
  6. additiondiluted with 2 l of hexane
  7. concentrationagain concentrated to a volume of about 1 l
  8. stirringstirred at -20° C. for a further 30 minutes
  9. filtrationThe precipitate was filtered off under suction
  10. washrinsed well with 700 ml of cold (-20° C.) hexane
  11. customThe filtrate was freed from solvent on a rotary evaporator
  12. filtrationthe resulting yellow oil (195 g) was filtered chromatographically on silica gel with about 3 l of hexane
  13. customThe eluate was evaporated up to constant weight on a rotary evaporator, there

Sources & evidence

ORD record
ord-f19ebf64f9794270aedde1ace21981a7
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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