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

HRID 855569Notes

Reaction equation

HRID 855569 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 (×3). The combined organic layer was washed with H2O (×2) 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 (×3)
  2. washThe combined organic layer was washed with H2O (×2) 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-ecb292ddf80d46aebca7410a7911699b
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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