Hydrogen Bromide → 1-(3-Bromopropyl)-4-methylbenzene

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.[BrH:12]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:12])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 2218933-(4-Methylphenyl)propan-1-ol

Product 1

HCID 140848591-(3-Bromopropyl)-4-methylbenzene

Procedure

3-(4-Methylphenyl)propanol (2.13 g) was heated in 7 ml of 47% aqueous hydrobromic acid under reflux for 5 hours. The solvent was then distilled off under reduced pressure and, after addition of water, the residue was extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was distilled under reduced pressure to give 1.75 g of 3-(4-methylphenyl)propyl bromide. Boiling point: 65° C./0.7 mmHg.

Workup

temperatureunder reflux for 5 hours
distillationThe solvent was then distilled off under reduced pressure
additionafter addition of water
extractionthe residue was extracted with ether
washThe organic layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record: ord-fd1850b06e4b44c79be4d76efcef089e
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04987132

Reaction notes

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