1-Bromoadamantane → 1-PHENYLADAMANTANE

HRID 346097Notes

Reaction equation

HRID 346097 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.[Fe](Cl)(Cl)Cl>[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

4

Reactant 1

HCID 791061-Bromoadamantane

Product 1

HCID 5226961-PHENYLADAMANTANEYield 80%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 241BenzeneSolvent2×

Procedure

Heat 0.068 mol of iron(III) chloride to boiling in 20 ml of absolute benzene. Drop 0.0186 mol of 1-bromo-adamantane, dissolved in 30 ml of absolute benzene, to the solution. Then heat to boiling for 3 hrs. After cooling, pour the reaction mixture onto ice/hydrochloric acid, separate the organic phase, and extract the aqueous phase with two portions of benzene. Wash the combined organic phases with water, dry with calcium chloride, filter and evaporate to dryness under vacuum. Recrystallize the residue from methanol. (Yield: 80%).

Workup

  1. temperatureThen heat
  2. temperatureAfter cooling
  3. additionpour the reaction mixture onto ice/hydrochloric acid
  4. customseparate the organic phase
  5. extractionextract the aqueous phase with two portions of benzene
  6. washWash the combined organic phases with water
  7. dry with materialdry with calcium chloride
  8. filtrationfilter
  9. customevaporate to dryness under vacuum
  10. customRecrystallize the residue from methanol

Sources & evidence

ORD record
ord-c14d5d24600e465890c68224b72d0d8d
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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