Phosphorus tribromide → 2,4-Dichlorophenethyl bromide
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5]O.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][Br:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2,4-Dichlorophenethyl alcohol (10 g, 52.0 mmol) was dissolved in 100 mL of methylene chloride, cooled to 0° C. under nitrogen atmosphere and 1.5 equiv of phosphorous tribromide (1M in CH2Cl2, 80 mmol, 80 mL) was added dropwise. The resulting reaction mixture was warmed to 23° C. and stirred for 2 h before the very slow addition of 200 mL of saturated aqueous sodium bicarbonate and extraction with methylene chloride (2×150 mL). The combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by a SiO2 plug (5% EtOAc/hexanes) to yield 2,4-dichlorophenethyl bromide. The product was characterized by 1H NMR and HPLC.
Workup
- customThe resulting reaction mixture
- temperaturewas warmed to 23° C.
- dry with materialThe combined organic layers were dried over sodium sulfate
- customevaporated under reduced pressure
- customThe crude product was purified by a SiO2 plug (5% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-e0b689bd2075450489537fe25fbe17dd
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07411073B2
Reaction notes
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