Carbon tetrabromide → HCID 86587115, compound

HRID 2414589Notes

Reaction equation

HRID 2414589 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14].C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1712010Cis-11-tetradecenol

Product 1

HCID 86587115HCID 86587115, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Cis-11-tetradecen-1-ol (1 g, 4.72 mmol) and carbon tetrabromide (1.56 g 4.72 mmol) were dissolved in dichloromethane (3 ml) and the solution was cooled in ice bath. A solution of triphenylphosphine (1.24 g, 4.72 mmol) in 2 mL of dichloromethane was added dropwise. After stirring at 0° C. for 15 minutes and at room temperature for 3 h, the solvent was evaporated and the residue was diluted with ether. The ether solution was filtered and concentrated and purified using column chromatography on silica gel eluting with hexane:ethyl acetate (3:1) to give 0.23 g of (Z)-14-bromo-3-tetradecene.

Workup

  1. temperaturethe solution was cooled in ice bath
  2. customthe solvent was evaporated
  3. additionthe residue was diluted with ether
  4. filtrationThe ether solution was filtered
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-7f08110056094bc2998c988144b3525d
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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