Hydrogen Bromide → (5-Bromopentyl)benzene

HRID 1920586Notes

Reaction equation

HRID 1920586 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:13]>C(OCC)(=O)C>[Br:13][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 615235-Phenyl-1-pentanol

Product 1

HCID 285561(5-Bromopentyl)benzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 50 g (0.304 mmol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid, and the mixture is stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After complete conversion, the mixture is cooled to room temperature and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane). This gives 59.4 g (0.26 mol, 86% of theory) of a colorless liquid.

Workup

  1. stirringThe reaction solution is then stirred at 100° C. for 12 hours
  2. temperatureAfter complete conversion, the mixture is cooled to room temperature
  3. extractionAfter extraction
  4. customthe organic phase is separated off
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-bc4e4293e4844d01ab0ef93965cb7978
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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