Potassium Carbonate → 1-PHENYLADAMANTANE

HRID 1865039Notes

Reaction equation

HRID 1865039 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.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1C=CC=CC=1>[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 2

HCID 11430Potassium CarbonateHCID 791061-Bromoadamantane

Product 1

HCID 5226961-PHENYLADAMANTANE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Conditions

Temperature
120 °C

Procedure

Add 1-bromoadamantane (10 g, 46.5 mmols), potassium carbonate (7.7 g, 55.8 mmols) and palladium on carbon (250 mg, catalytic) in benzene and heat to 120° C. for 1 week. Cool the reaction to room temperature and filter over Celite® rinsing with EtOAc. Concentrate under reduce pressure to provide the title compound. 1H NMR (400 MHz; CDCl3) δ 7.2-7.4(m, 5H), 2.10(s, 3H), 1.92(s, 6H), 1.77(s, 6H).

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationfilter over Celite®
  4. washrinsing with EtOAc
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-165b889c4f324f28bb14ef21e29eab12
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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