2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 70873650, compound

HRID 2172189Notes

Reaction equation

HRID 2172189 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=O.[Cl:12][C:13]1[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19]([NH2:21])=[O:20])=[CH:15][CH:14]=1.CN1CCCC1=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]2[O:20][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=3)[N:21]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 13387N-methyl-2-pyrrolidoneHCID 970914-ChlorophenoxyacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 70873650HCID 70873650, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-1-(4-hydroxyphenyl)ethanone (2.90 g) and 2-(4-chlorophenoxy)acetamide (5.0 g) were added to N-methylpyrrolidone (5 ml), and the mixture was stirred at 100° C. under a nitrogen atmosphere. After being cooled to room temperature, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture and separated into layers. The organic layer was washed with water, dried over sodium sulfate, and then concentrated under reduced pressure. Sodium acetate (11.1 g) in DMF (20 ml) were added to the residue and then stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and the prepared insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1) and recrystallized from hexane-ethyl acetate to afford the title compound as a pale yellow powder (1.63 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customseparated into layers
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionSodium acetate (11.1 g) in DMF (20 ml) were added to the residue
  7. stirringstirred at room temperature for 2 hours
  8. additionThe reaction mixture was diluted with ethyl acetate
  9. customthe prepared insoluble matter was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)
  12. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-cc2f89af174245109a2e201b321ee7d1
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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