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

HRID 84059

Reaction equation

HRID 84059 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4]O.S(=O)(=O)(O)O.[BrH:17]>>[Br:17][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Conditions

Temperature
100 °C

Procedure

3,7-Dimethyloctan-1-ol (10.0 g, 63.2 mmol) was suspended in 48% aqueous hydrobromic acid solution, concentrated sulfuric acid (0.17 ml) was added dropwise and the mixture was stirred at 100° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, extracted with hexane (200 ml), and washed twice with 5% aqueous sodium hydrogen carbonate solution (100 ml) and once with 20% brine (100 ml). The organic layer was dried over sodium sulfate, and the solvent in the filtrate was evaporated to give the title compound (13.3 g, 95.1%) as a colorless oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with hexane (200 ml)
  3. washwashed twice with 5% aqueous sodium hydrogen carbonate solution (100 ml) and once with 20% brine (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent in the filtrate was evaporated

Sources & evidence

ORD record
ord-a59bb370680d405f82592bd4b5c44888
Source dataset
uspto-grants-2014_09
Patent number
US08846885B2

Linked notes

Loading…