Hydrogen Bromide → (5-Bromopentyl)benzene

HRID 1015924Notes

Reaction equation

HRID 1015924 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 mol) 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 the reaction has gone to completion, 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 and dried over sodium sulfate. After filtration, the filtrate is evaporated 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. temperaturethe mixture is cooled to room temperature
  3. extractionAfter extraction
  4. customthe organic phase is separated off
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-a2e904f7d94745838ac23febdede1b40
Source dataset
uspto-grants-2011_07
Patent number
US07985876B2

Reaction notes

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