3-(Dimethylamino)phenol → HCID 59418776, compound

HRID 2178266Notes

Reaction equation

HRID 2178266 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[CH3:8][N:9]([CH3:17])[C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]([O:4][CH2:5][CH2:6][O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([N:9]([CH3:17])[CH3:8])[CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 59418776HCID 59418776, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromoethyl acetate (1.34 g, 4.01 mmol) was added to a suspension of 3-(dimethylamino)phenol (0.50 g, 3.64 mmol) and K2CO3 (1.5 g, 10.8 mmol) in anhydrous DMF (3 mL). The reaction mixture was heated to 80° C. for 18 hours, cooled to rt, diluted with water, extracted with DCM. The organic phases were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 90:10-80:20, to provide the desired compound 2-(3-(dimethylamino)phenoxy)ethyl acetate (39A).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with DCM
  3. washThe organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-3f5f8479504347938277a6c69d37934b
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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