Hydrogen Bromide → 1-Bromo-3,7-dimethyloctane

HRID 2206356Notes

Reaction equation

HRID 2206356 reaction equation
S(=O)(=O)(O)O.[CH3:6][CH:7]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9]O.[BrH:17]>>[CH3:6][CH:7]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][Br:17]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 77923,7-Dimethyl-1-octanol

Product 1

HCID 1379141-Bromo-3,7-dimethyloctaneYield 82.1%

Procedure

48% HBr (200 ml) and concentrated sulfuric acid (0.46 ml) were added to 3,7-dimethyl-1-octanol (21.0 g, 157.9 mmol), and the mixture was heated overnight. After allowing to cool to room temperature, and the mixture was extracted with hexane. The organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried and concentrated to give the title compound (28.7 g, 82.1%).

Workup

  1. temperaturethe mixture was heated overnight
  2. extractionthe mixture was extracted with hexane
  3. washThe organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2afcddbb13724123b7246cb6ef59251b
Source dataset
uspto-grants-2016_06
Patent number
US09371353B2

Reaction notes

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