Benzyl Bromide → HCID 14784149, compound

HRID 1399959Notes

Reaction equation

HRID 1399959 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 104889843-Bromo-5-nitrophenol

Product 1

HCID 14784149HCID 14784149, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ii (770 g, 3.53 mol) in acetone (10 L) was added K2CO3 (2.45 kg, 17.75 mol) at RT followed by benzyl bromide (632 mL, 5.32 mol) over a period of 30 min. The mixture was stirred for 15 min and then heated at reflux for 3 h. The mixture was filtered through celite and the acetone was distilled off. The residue was purified over silica eluting with EtOAc:hexane (5:95) to obtain iii (551 g, 51%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. filtrationThe mixture was filtered through celite
  4. distillationthe acetone was distilled off
  5. customThe residue was purified over silica eluting with EtOAc:hexane (5:95)

Sources & evidence

ORD record
ord-0ce5549fe9654b2f94d7c1e5d27a3f3d
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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