Hexane → HCID 178442084, compound

HRID 370701Notes

Reaction equation

HRID 370701 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]([Br:24])(Br)Br.[CH2:25]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][C@H:44]3[CH2:49][CH2:48][C@H:47]([CH:50]=O)[CH2:46][CH2:45]3)=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:20][C:21]([Br:24])=[CH:50][C@H:47]1[CH2:48][CH2:49][C@H:44]([CH2:43][CH2:42][C:39]2[CH:38]=[CH:37][C:36]([C:33]3[CH:34]=[CH:35][C:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:31][CH:32]=3)=[CH:41][CH:40]=2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178442087HCID 178442087, compound

Product 1

HCID 178442084HCID 178442084, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 6.7 g of triphenylphosphine in 60 ml of methylene chloride was placed at -20° C. under argon gasification in a sulphonation flask equipped with a thermometer, dropping funnel and solid substance addition tube and treated within 5 minutes with 4.3 g of tetrabromomethane. The clear orange solution was stirred at -15° C. for a further 10 minutes and then a solution of 2.33 g of trans-4-[2-(4'-pentyl-4-biphenylyl)ethyl]cyclohexanecarboxaldehyde in 40 ml of methylene chloride was added dropwise at -5° C. within 10 minutes. The mixture was stirred at -5° C. for a further 10 minutes, then poured into 700 ml of hexane and freed from precipitated triphenylphosphine oxide by filtration. The concentrated filtrate was digested with 300 ml of hexane, filtered and concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.5 g) on silica gel with 1% ethyl acetate/petroleum ether gave 2.87 g (87%) of 4-[2-[trans-4-(2,2-dibromovinyl)cyclohexyl]ethyl]-4'-pentylbiphenyl as colourless crystals.

Workup

  1. customwas placed at -20° C. under argon
  2. customequipped with a thermometer
  3. additionfunnel and solid substance addition tube
  4. stirringThe mixture was stirred at -5° C. for a further 10 minutes
  5. customfrom precipitated triphenylphosphine oxide
  6. filtrationby filtration
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5ddb945da66b4327a0a9424dc2a64b9c
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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