Pentane → HCID 178444401, compound

HRID 370675Notes

Reaction equation

HRID 370675 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:38]2[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=2)[CH2:32][CH2:31]1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCC>C(Cl)Cl.[Zn]>[Br:1][C:2]([Br:5])=[CH:42][C:41]1[CH:44]=[CH:45][C: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)=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444410HCID 178444410, compound

Product 1

HCID 178444401HCID 178444401, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 13.27 g of tetrabromomethane, 10.49 g of triphenylphosphine and 2.62 g of zinc dust in 100 ml of methylene chloride was stirred at room temperature for 24 hours in a sulphonation flask under argon gasification. In so doing, the heterogeneous mixture changed in colour via yellow-green to dark violet and pale violet. A solution of 2.86 g of p-[2-(trans-4-pentylcyclohexyl)ethyl]benzaldehyde in 10 ml of methylene chloride was subsequently added dropwise, the mixture was stirred at room temperature for 4 hours and then poured into 700 ml of pentane. The voluminous precipitate which separated was filtered off (rinsing with pentane), the concentrated filtrate (5.25 g) was digested with 300 ml of pentane, filtered and concentrated. Low-pressure chromatography (0.5 bar) of the residue (4.8 g) on silica gel with 3% ethyl acetate/petroleum ether gave 3.13 g (71%) of β,β-dibromo-p-[2-(trans-4-pentylcyclohexyl)ethyl]styrene as colourless crystals (purity 99.8%); m.p. 47.3° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. customThe voluminous precipitate which separated
  3. filtrationwas filtered off
  4. wash(rinsing with pentane)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aae3bab99963428d81e8a3078657022e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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