Carbon tetrabromide → 13-Bromotridec-1-ene
Reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([Br:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 12-tridecen-1-ol (2.11 g, 10.7 mmol) and carbon tetrabromide (4.37 g, 13.1 mmol) in dichloromethane (15 mL) at 0° C. was added triphenyl phosphine (3.45 g, 13.1 mmol) in portions over 5 minutes. After stirring for 1.5 hours at 25° C. the solvent was evaporated and the residue extracted with hexane (3×30 mL), filtering off any solids. The solvent was evaporated to afford 12-tridecenyl bromide as a clear oil which was used without further purification.
Workup
- customwas evaporated
- extractionthe residue extracted with hexane (3×30 mL)
- filtrationfiltering off any solids
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-a79d650b2d2d41f3be6097ee48072202
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866576
Reaction notes
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