Benzyl Bromide → HCID 14784149, compound

HRID 712146Notes

Reaction equation

HRID 712146 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 3-bromo-5-nitro-phenol (770 g, 3.53 mol) in acetone (10 L) was added pulverized K2CO3 (2.45 kg, 17.75 mol) in one portion at rt followed by addition of benzyl bromide (632 mL, 5.32 mol) over a period of 30 min. The resulting reaction mixture was stirred for 15 min then heated at reflux for 3 h. After reaction completion (by TLC), the reaction mixture was filtered through celite and the acetone distilled off. The crude residue thus obtained was purified over silica gel (60-120 M) using EtOAc:hexane (5:95) to obtain the desired product (551 g, 51%).

Workup

  1. customat rt
  2. customThe resulting reaction mixture
  3. temperaturethen heated
  4. temperatureat reflux for 3 h
  5. customAfter reaction completion (by TLC)
  6. filtrationthe reaction mixture was filtered through celite
  7. distillationthe acetone distilled off
  8. customThe crude residue thus obtained
  9. customwas purified over silica gel (60-120 M)

Sources & evidence

ORD record
ord-c3c5112d04e34992a02df5f456b13ae7
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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