Potassium Carbonate → HCID 54563713, compound

HRID 846474Notes

Reaction equation

HRID 846474 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:17][C:16]=1[OH:28].[F:29][C:30]1[CH:37]=[C:36]([Br:38])[CH:35]=[CH:34][C:31]=1[CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C=O)C>[F:29][C:30]1[CH:37]=[C:36]([Br:38])[CH:35]=[CH:34][C:31]=1[CH2:32][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:17][C:16]=1[OH:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 21734064HCID 21734064, compound

Product 1

HCID 54563713HCID 54563713, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5 ml of a DMF solution containing 200 mg (0.5181 mmol) of 2,2'-dihydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl and 716.7 μl (5.181 mmol) of 2-fluoro-4-bromobenzylbromide, there was added 85.8 mg (0.6217 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated for 1 hour at room temperature. The reaction mixture was filtered by suction through Celite to remove the solid matter and the filtrate was washed with ethyl acetate. After the solvent in the filtrate was evaporated off under reduced pressure, the evaporated residue was dissolved in chloroform. This solution was washed with dilute hydrochloric acid, water and aequeous sodium bicarbonate, water and aqueous sodium cholride solution in this sequene and was dried by adding anhydrous sodium sulfate. The residue obtained after the solvent had been evaporated off was purified by silica gel column chromatography (with 50 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1 and 50/1) to obtain 212.4 mg (0.3706 mmol, 72%) of 2-(2-fluoro-4-bromobenzyloxy)-2'-hydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl as an oily product.

Workup

  1. filtrationThe reaction mixture was filtered by suction through Celite
  2. customto remove the solid matter
  3. washthe filtrate was washed with ethyl acetate
  4. customAfter the solvent in the filtrate was evaporated off under reduced pressure
  5. dissolutionthe evaporated residue was dissolved in chloroform
  6. washThis solution was washed with dilute hydrochloric acid, water and aequeous sodium bicarbonate, water and aqueous sodium cholride solution in this sequene
  7. customwas dried
  8. additionby adding anhydrous sodium sulfate
  9. customThe residue obtained after the solvent
  10. customhad been evaporated off
  11. customwas purified by silica gel column chromatography (with 50 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1 and 50/1)

Sources & evidence

ORD record
ord-6411c5ee7d1e43bfa6a958fae4049d4f
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

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