Carbon tetrabromide → 9-Octadecene, 1-bromo-, (9Z)-

HRID 1596157Notes

Reaction equation

HRID 1596157 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20](O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[Br:39]C(Br)(Br)Br>C(#N)C>[CH2:20]([Br:39])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5284499Oleyl Alcohol

Product 1

HCID 58403839-Octadecene, 1-bromo-, (9Z)-Yield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine (2.52 g; 9.62 mmol) is added portionwise to a vigorously stirred solution of oleyl alcohol (1.00 g; 3.72 mmol; Fluka, 99%) and tetrabromomethane (1.61 g; 4.84 mmol) in acetonitrile (15 ml) at 0° C. The heterogeneous medium is stirred for 1 h at room temperature. The supernatant is then transferred into a round-bottomed flask and the residual paste is triturated with ether (10 ml) and then filtered. The combined organic solutions are concentrated under reduced pressure to give a colorless oil which is purified by chromatography on a column of silica gel (eluent: hexane) to give oleyl bromide (1.21 g; 98%) in the form of a colorless oil.

Workup

  1. customThe supernatant is then transferred into a round-bottomed flask
  2. customthe residual paste is triturated with ether (10 ml)
  3. filtrationfiltered
  4. concentrationThe combined organic solutions are concentrated under reduced pressure
  5. customto give a colorless oil which
  6. customis purified by chromatography on a column of silica gel (eluent: hexane)

Sources & evidence

ORD record
ord-04e16c1024e848739fabc8651e252792
Source dataset
uspto-grants-2001_09
Patent number
US06291423B1

Reaction notes

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