Dichloromethane → Methyl 9-oxoxanthene-3-carboxylate

HRID 733048Notes

Reaction equation

HRID 733048 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(N(CC)CC)C.C(Cl)Cl.[CH3:27][OH:28].CN([CH:32]=[O:33])C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:27][O:28][C:32]([C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:33]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2316083-Bromo-9H-xanthen-9-oneHCID 21901440N,N-dimethylformamide methanol

Product 1

HCID 473475Methyl 9-oxoxanthene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

A sample of Compound 3a (20 g, 72.2 mmol) was dissolved in a 2:1 MeOH/DMF solution (600 mL). To this solution was added triethylamine (40 mL, 290 mmol) and the solution was degassed with Argon. To this was added dichlorobis(triphenylphosphine)palladium (II) (2.0 g, 2.85 mmol), and the reaction was transferred to a bomb and charged with 150 psi of CO (g). The reaction was stirred at 90° C. for 24 h. Upon completion, the reaction was cooled to 40° C. and CH2Cl2 was added. The reaction was filtered while warm and evaporated to provide the crude product. Recrystallization from ethanol gave 16.62 g (65.4 mmol) of Compound 4a. MS m/z (MH+) 255.

Workup

  1. customthe solution was degassed with Argon
  2. additioncharged with 150 psi of CO (g)
  3. temperatureUpon completion, the reaction was cooled to 40° C.
  4. filtrationThe reaction was filtered
  5. temperaturewhile warm
  6. customevaporated
  7. customto provide the crude product
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-fe368bc807c94e048d11728906491261
Source dataset
uspto-grants-2009_09
Patent number
US07589103B2

Reaction notes

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