Hydrogen Bromide → Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

HRID 1414199Notes

Reaction equation

HRID 1414199 reaction equation
[BrH:1].[C:2]12([CH2:12][OH:13])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2>[Br-].[Zn+2].[Br-].O>[C:2]12([CH2:12][OH:13])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2.[C:2]12([CH2:12][Br:1])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

Product 2

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 14163041-(Bromomethyl)adamantane

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 962WaterSolvent

Procedure

To 39 g (0.17 moles) of zinc bromide, 29.8 g (0.17 mole) of hydrobromic acid were added. To the solution thus obtained, 11.5 g (0.069 mole) of 1-adamantyl methylalcohol which was prepared by the method shown in (1) was added and the mixture was refluxed for 11 hours. After the reaction mixture was brought to room temperature, 200 ml of water were added to this and extracted with two 300 ml portions of ether. After washing with 100 ml of water saturated with sodium bicarbonate and 100 ml of water, the resulting ether layer was dehydrated with anhydrous magnesium sulfate and was filtered. Ether was then distilled away. Residual solids were recrystallized from methanol or sublimed (1 mmHg, 75° C) to purify it, and 13 g of 1-adamantyl methyl bromide were obtained. Melting point of the product was 37°-39° C and the yield was 84%.

Workup

  1. customTo the solution thus obtained
  2. additionwas added
  3. temperaturethe mixture was refluxed for 11 hours
  4. customwas brought to room temperature
  5. extractionextracted with two 300 ml portions of ether
  6. washAfter washing with 100 ml of water saturated with sodium bicarbonate and 100 ml of water
  7. filtrationwas filtered
  8. distillationEther was then distilled away
  9. customResidual solids were recrystallized from methanol or sublimed (1 mmHg, 75° C)
  10. customto purify it

Sources & evidence

ORD record
ord-ad10f974559347c8a2d2a7019f6c71c1
Source dataset
uspto-grants-1977_01
Patent number
US04001223

Reaction notes

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