Benzyl Bromide → HCID 10802515, compound

HRID 564980Notes

Reaction equation

HRID 564980 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:13]([O:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[C:3]([CH3:12])[C:2]([Cl:1])=[CH:7][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 948764-Chloro-2-nitro-m-cresol

Product 1

HCID 10802515HCID 10802515, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.50 g (8.00 mmols) of 4-chloro-3-methyl-2-nitrophenol, 1.50 g (8.80 mmols) of benzyl bromide, 2.43 g (17.6 mmols) of potassium carbonate and 70 ml of acetone was refluxed for 2 hours. Thereafter insoluble matters were filtered off and the filtrate was concentrated under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 2.22 g (>99%) of 3-benzyloxy-6-chloro-2-nitrotoluene.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThereafter insoluble matters were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was isolated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8cb579e1f680477591c5c3f0efc2756e
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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