Hexane → HCID 178444390, compound

HRID 1982122Notes

Reaction equation

HRID 1982122 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:30]1[CH2:35][CH2:34][C@H:33]([CH:36]=O)[CH2:32][CH2:31]1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444538HCID 178444538, compound

Product 1

HCID 178444390HCID 178444390, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-5 °C

Procedure

A solution, cooled to -20° C., of 331.6 g of tetrabromomethane in 1 l of dry methylene chloride was treated dropwise under nitrogen gasification within 30 minutes with a solution of 524.6 g of triphenylphosphine in 1 l of methylene chloride. The mixture was subsequently stirred at -5° C. for a further 30 minutes, then treated dropwise at this temperature within 30 minutes with a solution of 91.2 g of trans-4-pentylcyclohexanecarboxaldehyde in 500 ml of methylene chloride and stirred at -5° C. for a further 2 hours. The mixture was poured into 6 l of hexane, the mixture was stirred at -20° C. for 1 hour and then the precipitate was filtered off under suction and washed well with about 1 l of cold (-20° C.) hexane. The filtrate was concentrated to a volume of about 1 l on a rotary evaporator, dilued with 2 l of hexane, again concentrated to a volume of about 1 l and stirred at -20° C. for a further 1 hour. The precipitate was filtered off under suction and rinsed well with about 500 ml of cold (-20° C.) hexane. The filtrate was freed from solvent on a rotary evaporator and the yellow oil obtained 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 122.8 g (72.6%) of trans-1-(2,2-dibromovinyl)-4-pentylcyclohexane as a colourless oil; Rf-value (hexane) 0.55.

Workup

  1. stirringstirred at -5° C. for a further 2 hours
  2. stirringthe mixture was stirred at -20° C. for 1 hour
  3. filtrationthe precipitate was filtered off under suction
  4. washwashed well with about 1 l of cold (-20° C.) hexane
  5. concentrationThe filtrate was concentrated to a volume of about 1 l on a rotary evaporator
  6. concentrationagain concentrated to a volume of about 1 l
  7. stirringstirred at -20° C. for a further 1 hour
  8. filtrationThe precipitate was filtered off under suction
  9. washrinsed well with about 500 ml of cold (-20° C.) hexane
  10. customThe filtrate was freed from solvent on a rotary evaporator
  11. customthe yellow oil obtained
  12. filtrationwas 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-ae3b8a46b2a14bf0998af1700cfd010c
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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