Potassium Carbonate → HCID 66696592, compound

HRID 1672548Notes

Reaction equation

HRID 1672548 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[N+:11]([CH:13](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:14])#[C-:12].C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:7][CH:12]=[N:11][C:13]=2[CH3:14])=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696592HCID 66696592, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-3-fluorobenzaldehyde (1.02 g, 5.0 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.05 g, 5.0 mmol), and K2CO3 (0.83 g, 6.0 mmol) in methanol (20 mL) was heated to reflux. After 2.5 hr the mixture was cooled to ambient temperature and the volatiles evaporated. The residue was partitioned between Et2O and H2O. The separated aqueous phase was extracted with Et2O, and the combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280™; 10% to 20% EtOAc/hexanes eluant; SF25-80 g column) yielded 1.04 g (81%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.41 (s, 1H), 7.83 (dd, J=8.3, 7.5 1H), 7.57 (dd, J=10.1, 2.0 1H), 7.42 (dd, J=8.5, 2.0 1H), 2.38 (s, 3H). MS (DCI+) m/z 256/258 (M+H).

Workup

  1. temperaturewas heated to reflux
  2. customthe volatiles evaporated
  3. customThe residue was partitioned between Et2O and H2O
  4. extractionThe separated aqueous phase was extracted with Et2O
  5. extractionthe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ee631e2dd9741ea9580af104b17c80b
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

Loading…