Water → HCID 58423836, compound

HRID 1408617Notes

Reaction equation

HRID 1408617 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12]1([C:18](=O)[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCC1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:18]([CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][C:8]2=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58423836HCID 58423836, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (64.2 g, 0.3 mol), 1-phenyl-ethanone (46.8 g, 0.39 mol) and pyrrolidine (6 g, 0.084 mol) in toluene (125 mL) was stirred vigorously at room temperature overnight. Then the mixture was refluxed for 6 h. After cooling, the mixture was treated with water (100 mL) and extracted with ethyl acetate (200 mL*3). The combined organic layers were concentrated and the residue was purified by column to give 6-bromo-2-methyl-2-phenyl-chroman-4-one (23.7 g, 25%). 1H-NMR (CDCl3): 1.74 (s, 3H), 3.06 (d, 1H), 3.31 (d, 1H), 6.95 (d, 1H), 7.20-7.37 (m, 5H), 7.52 (d, 1H), 7.84 (s, 1H).

Workup

  1. temperatureThen the mixture was refluxed for 6 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (200 mL*3)
  4. concentrationThe combined organic layers were concentrated
  5. customthe residue was purified by column

Sources & evidence

ORD record
ord-3a0e9e25038e47478ebbf157db4f926f
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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