1-Bromoadamantane → 1-PHENYLADAMANTANE

HRID 1714706Notes

Reaction equation

HRID 1714706 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2>C1C=CC=CC=1.O.FC(F)(F)S([O-])(=O)=O.[Ag+]>[C:2]1([C:2]23[CH2:11][CH:6]4[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]4)[CH2:3]2)[CH2:9]3)[CH:11]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 791061-Bromoadamantane

Product 1

HCID 5226961-PHENYLADAMANTANEYield 82%

Reagents, catalysts & solvents 3

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

Silver trifluoromethanesulfonate (5 g) and 50 ml of benzene were mixed, 4.2 g of 1-bromoadamantane dissolved in 50 ml of benzene was added thereto over 30 minutes, and the resulting mixture was stirred for 12 hours in a dark place. The obtained reaction solution was poured in 300 ml of water and extracted with hexane, and the organic phase was washed with water and saturated saline, dried and concentrated to obtain a crude product. This crude product was purified by column chromatography, as a result, 1.7 g of 1-phenyladamantane was obtained.

Workup

  1. additionwas added
  2. customThe obtained reaction solution
  3. extractionextracted with hexane
  4. washthe organic phase was washed with water and saturated saline
  5. customdried
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThis crude product was purified by column chromatography, as a result

Sources & evidence

ORD record
ord-623eaceec1ca4c0aa2a2d718369d523e
Source dataset
uspto-grants-2010_09
Patent number
US07799505B2

Reaction notes

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