Tri-o-tolylphosphine → HCID 67302023, compound

HRID 641231Notes

Reaction equation

HRID 641231 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1.[C:11]([NH:14][C:15](=[CH2:20])[C:16]([O:18][CH3:19])=[O:17])(=[O:13])[CH3:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]([NH:14][C:15](=[CH:20][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1)[C:16]([O:18][CH3:19])=[O:17])(=[O:13])[CH3:12]

Participants

7

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 27355555-Bromo-2-chloro-m-xylene

Product 1

HCID 67302023HCID 67302023, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere 30.0 g (136.7 mmol) 5-bromo-2-chloro-1,3-dimethylbenzene, 24.0 g (164.0 mmol) methyl 2-acetylamino-acrylate in 420 mL triethylamine and 200 mL acetonitrile were combined with 3.4 g (10.9 mmol) tri-o-tolyl-phosphane and 2.4 g (10.9 mmol) Pd(OAc)2 and stirred for 18 h at 80° C. The precipitate was suction filtered, the filtrate was evaporated down i. vac., combined with 800 mL DCM and 800 mL water, the organic phase was separated off and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was stirred with EtOAc, suction filtered and dried i. vac.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated down i
  3. customthe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. stirringwas stirred with EtOAc, suction
  6. filtrationfiltered
  7. customdried i

Sources & evidence

ORD record
ord-c4efdc39c5354f5ea32d64a4d35e1c93
Source dataset
uspto-grants-2010_04
Patent number
US07696196B2

Reaction notes

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