Water → 1-(3,5-Dichlorophenyl)-propyl bromide

HRID 2298162Notes

Reaction equation

HRID 2298162 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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 24408BromineHCID 145813153,5-Dichlorobenzenepropanol

Product 1

HCID 222470351-(3,5-Dichlorophenyl)-propyl bromideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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) δ 7.21 (m, 1H), 7.08 (m, 2H), 3.37 (t, 2H), 2.74 (t, 2H), 2.13 (m, 2H).

Workup

  1. temperaturewas warmed to room temperature
  2. extractionthe aqueous solution was extracted with CH2Cl2
  3. washThe organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (hexanes)

Sources & evidence

ORD record
ord-3c018c55d4264f0d8035c0655bd5cb9f
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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