Water → HCID 11688411, compound

HRID 131590Notes

Reaction equation

HRID 131590 reaction equation
Br[C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[C:8]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:21]1([O:20][C:8]2[C:9]3[O:10][C:11]4[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=4[C:2]=3[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 21105708HCID 21105708, compound

Product 1

HCID 11688411HCID 11688411, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Intermediate 2-bromo-4-cyclopentoxy-3-(p-nitrophenoxy)-benzaldehyde (500 mg, 1.09 mmol), anhydrous sodium carbonate (150 mg, 1.325 mmol) and palladium (II) acetate (25 mg, 0.096 mmol), in dimethylformamide (10 ml) are heated and stirred under nitrogen at 130° C. for 7 h. Water (90 ml) is added to the cooled reaction mixture and extracted with ethyl acetate (2×25 ml). The combined organic layer was washed with 5% hydrochloric acid followed by water and dried over anhydrous sodium sulfate to afford the product as a yellow solid (200 mg). mp: 230-240° C.

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. washThe combined organic layer was washed with 5% hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-c5c0153794f24a8f9f283fc164916f4b
Source dataset
uspto-grants-2008_06
Patent number
US07384962B2

Reaction notes

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