Water → 1-(3,5-Dichlorophenyl)-propyl bromide
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH2:28][CH2:29][CH2:30]O)[CH:24]=[C:25]([Cl:27])[CH:26]=1.[Br:32]Br.O>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:28]([Br:32])[CH2:29][CH3:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Triphenylphosphine (315 mg, 1.20 mmol) was added to a solution of 3-(3,5-dichlorophenyl)-propanol (200 mg, 0.98 mmol) in CH2Cl2 (20 mL). The reaction mixture was cooled to 0° C. and bromine (207 mg, 1.30 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and was warmed to room temperature. The reaction was poured into water and the aqueous solution was extracted with CH2Cl2. The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes) to afford the title compound (134 mg). 1H NMR (400 MHz, CDCl3) δ7.21 (m, 1H), 7.08 (m, 2H), 3.37 (t, 2H), 2.74 (t, 2H), 2.13 (m, 2H).
Workup
- temperaturewas warmed to room temperature
- extractionthe aqueous solution was extracted with CH2Cl2
- washThe organic solution was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe product was purified by flash chromatography (hexanes)
Sources & evidence
- ORD record
- ord-3fe5d98ae26e4debad322450958def35
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06344485B1
Reaction notes
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