Hexane → HCID 178444459, compound

HRID 370692Notes

Reaction equation

HRID 370692 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]([CH2:36][CH2:37][C@H:38]2[CH2:43][CH2:42][C@H:41]([CH:44]=O)[CH2:40][CH2:39]2)[CH2:32][CH2:31]1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:44][C@H:41]1[CH2:42][CH2:43][C@H:38]([CH2:37][CH2:36][C@H:33]2[CH2:32][CH2:31][C@H:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:35][CH2:34]2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444462HCID 178444462, compound

Product 1

HCID 178444459HCID 178444459, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-5 °C

Procedure

A solution of 4.4 g of tetrabromomethane in 80 ml of methylene chloride was placed at -15° C. in a sulphonation flask under argon gasification and treated within 5 minutes with a solution of 7.0 g of triphenylphosphine in 20 ml of methylene chloride. The clear deep orange solution was stirred at -5° C. for a further 10 minutes and then a solution of 1.95 g of the trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarboxaldehyde in 20 ml of methylene chloride was added dropwise within 10 minutes. The mixture was stirred at 0° C. for a further 30 minutes, then poured into 600 ml of hexane and the precipitate which thereby separated was filtered off (rinsing with hexane). The concentrated filtrate was digested with 300 ml of hexane, left to stand at 0° C. for 30 minutes, filtered (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.0 g) on silica gel with hexane gave 2.68 g (89.2%) of trans-1-(2,2-dibromovinyl)-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexane which contained about 10% of the corresponding epimeric cis compound in accordance with NMR spectroscopic analysis and which was used without additional purification.

Workup

  1. stirringThe mixture was stirred at 0° C. for a further 30 minutes
  2. customthe precipitate which thereby separated
  3. filtrationwas filtered off
  4. wash(rinsing with hexane)
  5. waitleft
  6. waitto stand at 0° C. for 30 minutes
  7. filtrationfiltered
  8. wash(rinsing with hexane)
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-06fb87ec3acf4481ad8e628440bc2e70
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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