Dimethylformamide → HCID 68002053, compound

HRID 2046064Notes

Reaction equation

HRID 2046064 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].CN(C=O)C.Br[CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH:22]2[CH2:25][CH:20]1[C:21]2([CH3:27])[CH3:26]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]3[CH2:25][CH:20]2[C:21]3([CH3:26])[CH3:27])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 108944-IodophenolHCID 24758Sodium hydrideHCID 190944812-(2-Bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Product 1

HCID 68002053HCID 68002053, compoundYield 190.4%

Procedure

To a stirred suspension of 4-iodophenol (0.5 g; 2.27 mmol) and 60% NaH (0.16 g, 2.3 mmol) in anhydrous DMF (5 ml) 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.5 g, 2.2 mmol) was added the and mixture was stirred for 3 h at room temperature. After addition of more of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.2 g) the mixture was stirred for additional 2 h, quenched with NH4Cl solution and diluted to 20 ml with EtOAc. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.61 g, 73%), as a colourless paste. 1H-NMR (CDCl3) 7.51 (d, 2H, J=8.91 Hz); 6.64 (d, 2H, J=8.88 Hz); 3.88 (t, 2H, J=3.21 Hz); 2.34-1.84 (m, 10H); 1.17 (s, 3H); 1.01 (s, 3H).

Workup

  1. additionwas added the and mixture
  2. stirringwas stirred for additional 2 h
  3. customquenched with NH4Cl solution
  4. additiondiluted to 20 ml with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-55d5f7f84dee4999b3e496c7891888a2
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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