Carbon tetrabromide → HCID 178444391, compound

HRID 1249309Notes

Reaction equation

HRID 1249309 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13]O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]C(Br)(Br)Br>ClCCl>[Br:34][CH2:13][CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444485HCID 178444485, compound

Product 1

HCID 178444391HCID 178444391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 20 g of 2-(trans-4-pentylcyclohexyl)ethanol, 27.5 g of triphenylphosphine and 350 ml of dichloromethane was treated portionwise while stirring at -30° C. over a period of 45 minutes under an inert gas atmosphere with 36.5 g of tetrabromomethane. The resulting mixture was then stirred at -20° C. for another 30 minutes and at room temperature for 5 hours. The mixture was subsequently concentrated and the residue was triturated with 500 ml of hexane. After cooling to 0° C., the precipitated triphenylphosphine oxide was filtered off and the filtrate was chromatographed on silica gel with hexane. The crude 1-bromo-2-(trans-4-pentylcyclohexyl)ethane obtained (29.0 g) was distilled at 92°-98° C./1.5 Torr. Yield: 21.9 g as a colourless oil.

Workup

  1. additionwas treated portionwise
  2. concentrationThe mixture was subsequently concentrated
  3. customthe residue was triturated with 500 ml of hexane
  4. temperatureAfter cooling to 0° C.
  5. filtrationthe precipitated triphenylphosphine oxide was filtered off
  6. customthe filtrate was chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-d8e670b43654405595edccbb3f0da322
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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