Water → (4-Bromopentyl)benzene

HRID 1995695Notes

Reaction equation

HRID 1995695 reaction equation
[Br:1]Br.P(Br)(Br)Br.[C:7]1([CH2:13][CH2:14][CH2:15][CH:16](O)[CH3:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C(Cl)Cl>[Br:1][CH:16]([CH2:15][CH2:14][CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 24614Phosphorus tribromideHCID 1027884-Hydroxy-1-phenylpentane

Product 1

HCID 20487411(4-Bromopentyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To phosphorous 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 (812 g.) in methylene 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 one 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 one 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-158e719e46204caeb83bfeea4303e9c8
Source dataset
uspto-grants-1983_09
Patent number
US04405626

Reaction notes

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