反应详情

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.

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