Phosphorus tribromide → 2-(1-Bromoethyl)naphthalene
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11](O)[CH3:12].P(Br)(Br)[Br:15]>C1(C)C=CC=CC=1>[Br:15][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1-(Naphthalen-2-yl)ethanol (2.0 g, 11.6 mmol) was dissolved in toluene (30 mL). The solution was cooled to 0° C. PBr3 (1.09 mL, 11.6 mmol) was added dropwise over 15 min. The reaction mixture was then brought up to room temperature and stirred for 1 h. The mixture was washed with K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo to give crude 2-(1-bromoethyl)naphthalene. This intermediate was used in the following step.
Workup
- customwas then brought up to room temperature
- washThe mixture was washed with K2CO3 solution
- extractionextracted with EtOAc (3×30 mL)
- washThe EtOAc layer was washed with brine
- dry with materialdried (MgSO4)
- customThe solvent was evaporated off in-vacuo
Sources & evidence
- ORD record
- ord-c95275107b41455b93d44705b6b3f67d
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283340B2
Reaction notes
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