Chloride → (4-Bromopentyl)benzene

HRID 614116Notes

Reaction equation

HRID 614116 reaction equation
P(Br)(Br)(Br)(Br)Br.[Br:7]Br.P(Br)(Br)Br.[C:13]1([CH2:19][CH2:20][CH2:21][CH:22](O)[CH3:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-]>C(Cl)Cl.O>[Br:7][CH:22]([CH2:21][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:23]

Participants

8

Reactant 5

HCID 312ChlorideHCID 24408BromineHCID 24614Phosphorus tribromideHCID 62678Phosphorus pentabromideHCID 1027884-Hydroxy-1-phenylpentane

Product 1

HCID 20487411(4-Bromopentyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To phosphorus pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (8.2 g.) in metnhylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for 1 hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringthe mixture stirred for 1 hour
  3. customthe methylene chloride layer separated
  4. extractionThe extraction
  5. washthe combined extracts washed with water, saturated sodium bicarbonate solution, brine
  6. dry with materialdried over magnesium sulfate
  7. customConcentration of the dried extracts gives 12.4 g

Sources & evidence

ORD record
ord-90152288bef84537a18b93ddf85ec911
Source dataset
uspto-grants-1979_03
Patent number
US04143139

Reaction notes

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