Benzyl Bromide → 4-Bromo-2-methyl-1-(phenylmethoxy)benzene

HRID 1486519Notes

Reaction equation

HRID 1486519 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenol

Product 1

HCID 226368474-Bromo-2-methyl-1-(phenylmethoxy)benzeneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 4-bromo-2-methylphenol (1.25 g, 6.67 mmol) in 20 ml MeCN were added dry K2CO3 (1.84 g, 13.34 mmol, 2 equiv) and benzylbromide (0.872 ml, 7.34 mmol, 1.1 equiv) and reaction is stirred for 24 h at room temperature. Reaction mixture was filtered through Celite, solution was concentrated and purified by silica gel column chromatography (Hexane to 8% EtOAc/Hexane) to give 1.65 g 17 in 89% yield. Rf=0.90 (20% EtOAc/Hexane);

Workup

  1. customReaction mixture
  2. filtrationwas filtered through Celite, solution
  3. concentrationwas concentrated
  4. custompurified by silica gel column chromatography (Hexane to 8% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ea427bd705c84ba29d74b3749fe28e82
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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