Benzyl Bromide → N,N-bis-(2-hydroxyethyl)-2-fluoro-4-benzyloxyaniline

HRID 1875462Notes

Reaction equation

HRID 1875462 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:13][CH2:14][OH:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12].[OH-].[K+].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1>CCO>[OH:1][CH2:2][CH2:3][N:4]([CH2:13][CH2:14][OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:24][C:21]2[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=2)=[CH:7][C:6]=1[F:12]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 10822558HCID 10822558, compound

Product 1

HCID 10733374N,N-bis-(2-hydroxyethyl)-2-fluoro-4-benzyloxyanilineYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N,N-bis-(2-hydroxyethyl)-2-fluoro-4-hydroxyaniline (2 g) and KOH (0.64 g, 10.0 mmole) in EtOH (13 mL) was added BnBr (1.1 mL, 9.1 mmole) and the reaction mixture stirred at reflux for 3 h. The reaction mixture was cooled, evaporated to in dryness and purified by silica gel chromatography (0-7% MeOH/DCM) to provide N,N-bis-(2-hydroxyethyl)-2-fluoro-4-benzyloxyaniline (2.26 g) as a yellow syrup.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to in dryness
  4. custompurified by silica gel chromatography (0-7% MeOH/DCM)

Sources & evidence

ORD record
ord-2c722b48590c41eca595222f12c29fa8
Source dataset
uspto-grants-2012_11
Patent number
US08309554B2

Reaction notes

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