Hydrogen Bromide → 2,6-Diethyl-4-methylbenzyl bromide

HRID 385240Notes

Reaction equation

HRID 385240 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5]O)[CH3:2].[BrH:14]>>[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5][Br:14])[CH3:2]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 667075402,6-Diethyl-4-methylbenzyl alcohol

Product 1

HCID 669547062,6-Diethyl-4-methylbenzyl bromideYield 89%

Procedure

14.7 g (82.5 mmol) of 2,6-diethyl-4-methylbenzyl alcohol in 150 ml of hydrobromic acid are stirred at 100° C. for 4 h. After cooling, the mixture is extracted with dichloromethane and the extract is washed with water, dried (magnesium sulphate) and concentrated using a rotary evaporator. Distillation (110° C. bath temperature, 0.3 mbar) gives 17.82 g (89%) of 2,6-diethyl-4-methylbenzyl bromide as a colourless oil. 1H-NMR (400 MHz, CDCl3): δ=1.28 (t, 6H), 2.30 (s, 3H), 2.73 (q, 4H), 4.61 (s, 2H), 6.90 (s,

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with dichloromethane
  3. washthe extract is washed with water
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. distillationDistillation (110° C. bath temperature, 0.3 mbar)

Sources & evidence

ORD record
ord-80a1195f62aa457c923a77f350342768
Source dataset
uspto-grants-2013_02
Patent number
US08367873B2

Reaction notes

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