Potassium Carbonate → HCID 68684502, compound

HRID 1994103Notes

Reaction equation

HRID 1994103 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[CH:9]=1.[Cl:17][C:18]1[CH:19]=[C:20]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:14][C:11]1[CH:12]=[CH:13][C:8](/[CH:31]=[CH:30]/[C:29]([NH:28][C:20]2[CH:21]=[CH:22][C:23]([C:24]([F:25])([F:26])[F:27])=[C:18]([Cl:17])[CH:19]=2)=[O:32])=[CH:9][C:10]=1[O:15][CH3:16]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27695675-Bromo-2-chloroanisoleHCID 68686067HCID 68686067, compound

Product 1

HCID 68684502HCID 68684502, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of K2CO3 (0.936 g, 6.77 mmol) and n-Bu4NCl (0.753 g, 2.71 mmol) in DMF under an atmosphere of argon were added 4-bromo-1-chloro-2-methoxybenzene (0.600 g, 2.71 mmol), the amide from Step 1 (0.809 g, 3.25 mmol), and molecular sieves. The mixture was stirred for 10 min at rt before adding PPh3 (0.071 g, 0.271 mmol) and Pd(OAc)2 (0.0304 g, 0.135 mmol). The reaction mixture was heated at 80° C. overnight and then cooled to rt and filtered through Celite. The filtrate was diluted with EtOAc and washed with sat. NaHCO3 solution, water, and brine. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give the desired acrylamide (0-0.755 g, 72%).

Workup

  1. temperatureThe reaction mixture was heated at 80° C. overnight
  2. temperaturecooled to rt
  3. filtrationfiltered through Celite
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with sat. NaHCO3 solution, water, and brine
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5d79470b6c5f4c3f962017d8187275b2
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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