4-Iodophenol → 2-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

HRID 710351Notes

Reaction equation

HRID 710351 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][C:12]1[CH:13]2[CH2:18][CH:15]([CH2:16][CH:17]=1)[C:14]2([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][C:12]2[CH:13]3[CH2:18][CH:15]([CH2:16][CH:17]=2)[C:14]3([CH3:19])[CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 202771482-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene2×

Product 1

HCID 667267162-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-eneYield 28.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-iodophenol (0.4 g; 1.82 mmol), 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.45 g, 1.97 mmol) and K2CO3 (0.3 g, 2.17 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature. Another portion of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.3 g) was added and stirring was continued for 6 h. The mixture was diluted to 50 ml with EtOAc and washed with H2O (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the title product (0.189 g; 28%), as pale paste. 1H-NMR (CDCl3) 0.81 (s, 3H); 1.26 (s, 3H); 2.06-2.44 (m, 8H); 3.91 (tr, 2H, J=6.97 Hz); 5.32 (s, 1H); 6.64 (d, 2H, J=8.96 Hz); 7.51 (d, 2H, J=8.96 Hz).

Workup

  1. stirringstirring
  2. waitwas continued for 6 h
  3. washwashed with H2O (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-98d837e8d00a431dbda479b6a2edd2d8
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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