N-bromobutanimide → 4-Bromo-2-methyl-1-((2-methylbenzyl)oxy)benzene

HRID 1993046Notes

Reaction equation

HRID 1993046 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>C(Cl)(Cl)(Cl)Cl>[CH3:9][C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Br:8])=[CH:16][C:15]=1[CH3:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 521469551-Methyl-2-((2-methylphenoxy)methyl)benzene

Product 1

HCID 591327494-Bromo-2-methyl-1-((2-methylbenzyl)oxy)benzeneYield 29.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

NBS (1.46 g, 8.23 mmol) was added to a solution of 31.1 (1.59 g, 7.48 mmol) in carbon tetrachloride (8 mL). The reaction was stirred at 60° C. overnight and filtered to remove succinimide. The filtrate was concentrated in vacuo and purified via radial chromatography (15% diethyl ether in hexanes) to yield 0.65 g (25%) of 2-(2-methyl-benzyloxy)-5-bromotoluene (31.2). LC/MSD m/e: 314.2 (M+Na).

Workup

  1. filtrationfiltered
  2. customto remove succinimide
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified via radial chromatography (15% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-e27afddfdb2c452eb9452a90b4d6e009
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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