Hydrogen Bromide → (5-Bromopentyl)benzene

HRID 1672627Notes

Reaction equation

HRID 1672627 reaction equation
[BrH:1].[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C>[Br:1][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 615235-Phenyl-1-pentanol

Product 1

HCID 285561(5-Bromopentyl)benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 416.7 ml (1.83 mol) 48% strength hydrobromic acid is mixed with 50 g (0.304 mol) of 5-phenylpentan-1-ol at 0° C. and stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After reaction is complete, 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 is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% yield) of a colorless liquid are obtained.

Workup

  1. stirringThe reaction solution is then stirred at 100° C. for 12 hours
  2. customAfter reaction
  3. temperaturethe mixture is cooled to room temperature
  4. extractionAfter extraction
  5. customthe organic phase is separated off
  6. washwashed with saturated sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate is is concentrated to dryness
  10. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane)

Sources & evidence

ORD record
ord-0745fdce428e42d398583bb5076a7f9a
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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