Hydrogen Bromide → (5-Bromopentyl)benzene

HRID 1913758Notes

Reaction equation

HRID 1913758 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)benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

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 at 0° C., and the mixture is stirred at 0° C. for 30 min. The reaction solution is subsequently stirred at 10° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and mixed with 200 ml of ethyl acetate. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. After filtration, the filtrate is evaporated 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 colourless liquid are obtained.

Workup

  1. stirringThe reaction solution is subsequently stirred at 10° 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 sulphate
  8. filtrationAfter filtration
  9. customthe filtrate is evaporated to dryness
  10. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane)

Sources & evidence

ORD record
ord-4e5cb9f8983f4765bdcc9965173aff13
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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