Hydrogen Bromide → 1-(2-Bromoethyl)adamantane

HRID 1892883Notes

Reaction equation

HRID 1892883 reaction equation
S(=O)(=O)(O)O.[BrH:6].[C:7]12([CH2:17][CH2:18]O)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>>[Br:6][CH2:18][CH2:17][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol

Product 1

HCID 14163051-(2-Bromoethyl)adamantane

Procedure

In a 1 l—roundbottom flask equipped with a reflux condenser 164 g concentrated sulphuric acid and 200 g hydrobromic acid (48% in water) were added subsequently under cooling with an ice bath to 126.20 g (0.70 mole) 2-(1-adamantyl)ethanol. The mixture was refluxed for 6 h and after cooling to room temperature given to 400 g of ice. The aqueous phase was extracted with 400 ml pentane. The organic layer was washed with a 2 M NaOH-solution and with water, dried over magnesium sulphate, and the solvent was removed in vacuo. The product was distilled in vacuo to yield 153.2 g (90%) of (1-(2-Bromo-ethyl)-adamantane as a colourless oil. 1H-NMR (400 MHz, CDCl3): δ=3.29 (t, 2H, CH2Br), 1.71 (t, 2H, CCH2CH2Br), 1.56-1.17 (m, 15H, aliphatic) ppm.

Workup

  1. additionwere added subsequently
  2. temperatureThe mixture was refluxed for 6 h
  3. extractionThe aqueous phase was extracted with 400 ml pentane
  4. washThe organic layer was washed with a 2 M NaOH-solution and with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. distillationThe product was distilled in vacuo

Sources & evidence

ORD record
ord-bef1549745954cc7b5a992389c3c23f6
Source dataset
uspto-grants-2013_08
Patent number
US08507706B2

Reaction notes

Loading…