Water → HCID 67365624, compound

HRID 410033Notes

Reaction equation

HRID 410033 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[OH:18])=[O:10])=[CH:4][CH:3]=1.[C:19]([Cu])#[N:20].O.CCOC(C)=O>CN(C=O)C>[OH:18][C:12]1[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=1[C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]#[N:20])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 20634662-(4-bromophenyl)-1-(2,4-dihydroxyphenyl)ethanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 67365624HCID 67365624, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-bromophenyl)-1-(2,4-dihydroxyphenyl)ethanone (5 g, 16.3 mmol) and CuCN (5.8 g, 65.4 mmol) in DMF (50 ml) was stirred at 150° C. for 6 h under nitrogen. Water (100 ml) and EtOAc (100 ml) was added to the mixture. The precipitate was filtered off and the filtrate was washed with brine (100 ml), dried over Na2SO4 and concentrated to give black oil, which was purified by Combiflash (PE/EtOAc=3/1) to afford product as a yellow powder (1.5 g, 36.6%). MS (ESI): m/z 254.1 [M+1]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe filtrate was washed with brine (100 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give black oil, which
  6. customwas purified by Combiflash (PE/EtOAc=3/1)

Sources & evidence

ORD record
ord-458c6cce88584a54bc48bba5c5acdb3a
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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