Benzyl Bromide → HCID 58566740, compound

HRID 2069667Notes

Reaction equation

HRID 2069667 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][N:10]([CH3:12])[CH3:11].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH2:9][N:10]([CH3:12])[CH3:11])[CH:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 43400074-Bromo-3-((dimethylamino)methyl)phenol

Product 1

HCID 58566740HCID 58566740, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-3-((dimethylamino)methyl)phenol (4 g, 17.4 mmol), benzylbromide (2 eq.), and potassium carbonate (3 eq.) in DMF (100 mL) was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford 1-(5-(benzyloxy)-2-bromophenyl)-N,N-dimethylmethanamine (709) (98%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e6760b47ea124317ba4677658119d8e2
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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