O-Cresol → 1-(2-Bromoethoxy)-2-methylbenzene

HRID 271228Notes

Reaction equation

HRID 271228 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].[Br:11][CH:12](Br)[CH3:13].S([O-])(O)(=O)=O.C([NH3+])(C)(C)C>>[Br:11][CH2:12][CH2:13][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 4

HCID 335O-CresolHCID 112011,1-DibromoethaneHCID 14798Sodium Hydroxide2×HCID 24996679t-Butylammonium hydrogen sulfate

Product 1

HCID 16225721-(2-Bromoethoxy)-2-methylbenzene

Procedure

2-Methyl-phenol (1 g, 9.25 mmol) in NaOH (aq) (3.24 mL, 12.96 mmol, 4M soln.) was treated with dibromoethane (2.74 mL, 31.7 mmol) and t-butylammoniumhydrogen sulfate (catalytic), and then placed in a Robbins™ oven at 99° C. for 72 hours. The pH was then adjusted to ˜8 with NaOH (4M aq. soln.) and the product extracted with CH2Cl2 (x3). The combined organic layer was washed with H2O (x2) and brine, dried over MgSO4. The resulting oil taken up in 4:1 hexane/EtOAc and passed through a plug of silica gel. The plug was then washed with 4:1 hexane/EtOAc and the filtrate concentrated to provide crude 2-bromo-1-(2-methylphenoxy)ethane.

Workup

  1. extractionthe product extracted with CH2Cl2 (x3)
  2. washThe combined organic layer was washed with H2O (x2) and brine
  3. dry with materialdried over MgSO4
  4. washThe plug was then washed with 4:1 hexane/EtOAc
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-21e6a719f0544b869f90d556cdfe0898
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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