Potassium Carbonate → HCID 57501699, compound

HRID 601500Notes

Reaction equation

HRID 601500 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23]>CN(C=O)C>[CH3:23][O:22][CH:21]([O:24][CH3:25])[CH2:20][O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 57501699HCID 57501699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an oven-dried round bottom flask, add 2-methoxy-4-nitro-phenol (2.45 g, 14.5 mmol) and purge with nitrogen. Add DMF (25 mL) by syringe, followed by K2CO3 (3.0 g, 21.7 mmol) and KI (catalytic) neat. Stir 30 min at room temperature and add 2-bromo-1,1-dimethoxy-ethane (1.9 mL, 15.9 mmol) by syringe. Attach a reflux condenser and stir overnight in a 120° C. oil bath. Quench with water, extract with ether (3×), dry over MgSO4, filter and concentrate under vacuum. Add xylenes and concentrate again under vacuum. Purify by flash chromatography on silica gel using a gradient of EtOAc/hexane (20% to 60%) to give the title compound as a white residue (2.55 g, 68%). Exact mass=257.1, MS (ES+) 258.2 (M+1)+. 1H NMR (CDCl3): δ 7.88 (dd, J=9.1, 2.8 Hz, 1H), 7.74 (d, J=2.8 Hz, 1H), 6.94 (d, J=9.1 Hz, 1H), 4.77 (t, J=5.2 Hz, 1H), 4.13 (d, J=4.9 Hz, 2H), 3.93 (s, 3H), 3.48 (s, 6H).

Workup

  1. custompurge with nitrogen
  2. stirringstir overnight in a 120° C. oil bath
  3. customQuench with water
  4. extractionextract with ether (3×)
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. concentrationAdd xylenes and concentrate again under vacuum
  9. customPurify by flash chromatography on silica gel using a gradient of EtOAc/hexane (20% to 60%)

Sources & evidence

ORD record
ord-8a1624ef682f4108b9bdba93c096bcaf
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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