Carbon tetrabromide → HCID 22251864, compound

HRID 1950693Notes

Reaction equation

HRID 1950693 reaction equation
[CH3:1][CH:2](O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:18][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 96687Pentadecan-2-ol

Product 1

HCID 22251864HCID 22251864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Pentadecanol of Example 5 (180 g) and dichloromethane (2500 ml) were added to a 5-litre three-necked flask. The mixture was cooled to 0° C., and carbon tetrabromide (313.6 g) was added and stirred until it dissolved. Triphenylphosphine (351.4 g) was then added dropwise. The resulting mixture was allowed to warm to ambient temperature and left stirring for two days. The reaction mixture was then filtered, and the solvent removed on a rotary evaporator at 56° C. The resulting solid was re-dissolved in heptane and left stirring for two days. It was then filtered through celite under vacuum, and the heptane removed on a rotary evaporator at 78° C. to yield the title compound.

Workup

  1. dissolutiondissolved
  2. temperatureto warm to ambient temperature
  3. waitleft
  4. stirringstirring for two days
  5. filtrationThe reaction mixture was then filtered
  6. customthe solvent removed on a rotary evaporator at 56° C
  7. dissolutionThe resulting solid was re-dissolved in heptane
  8. waitleft
  9. stirringstirring for two days
  10. filtrationIt was then filtered through celite under vacuum
  11. customthe heptane removed on a rotary evaporator at 78° C.

Sources & evidence

ORD record
ord-00c58e709ca84106ace29d99c319832b
Source dataset
uspto-grants-2013_03
Patent number
US08404627B2

Reaction notes

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