Potassium Carbonate → HCID 58579883, compound

HRID 2059870Notes

Reaction equation

HRID 2059870 reaction equation
Cl[CH2:2][C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:2][C:3]([N:5]([O:7][CH3:8])[CH3:6])=[O:4])=[C:12]([O:17][CH3:18])[CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2622344-Bromo-2-methoxyphenolHCID 27347162-Chloro-N-methoxy-N-methylacetamide

Product 1

HCID 58579883HCID 58579883, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-N-methoxy-N-methylacetamide (2.7 g, 19.63 mmol), 4-bromo-2-methoxyphenol (3.98 g, 19.63 mmol), and potassium carbonate (5.43 g, 39.3 mmol) in DMF (20 mL) was heated at 60° C. for 1 hour and stirred at RT overnight (16 hours). The reaction mixture was diluted with CH2Cl2, washed with sat NaHCO3, brine and dried (Na2SO4). After concentration, the crude product was purified by ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 0:100 gradient) to afford 2-(4-bromo-2-methoxyphenoxy)-N-methoxy-N-methylacetamide 16A (4.86 g, 15.98 mmol, 81% yield) as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ 6.97-7.04 (2H, m), 6.76 (1H, d, J=8.03 Hz), 4.86 (2H, s), 3.87 (3H, s), 3.75 (3H, s), 3.23 (3H, s).

Workup

  1. washwashed
  2. dry with materialdried (Na2SO4)
  3. concentrationAfter concentration
  4. customthe crude product was purified by ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 0:100 gradient)

Sources & evidence

ORD record
ord-b6b24d282b394578982dfb1a8d9f9a6e
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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