Reaction #47423

Reaction equation

hydrogen peroxide

2,6-difluoro-3-isopropoxy-phenylboronic acid

acetic acid

→

2,6-difluoro-3-isopropoxy-phenol

Yield 100.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherto come to room temperature
3. 3
   OtherThe mixture was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
5. 5
   Washwashed with hydrochloric acid (0.5N), water and brine
6. 6
   OtherThe organic phase was dried
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated which

Procedure

To a solution of 2,6-difluoro-3-isopropoxy-phenylboronic acid (10.0 g, 0.046 mol) in tetrahydrofuran (160 mL) was added glacial acetic acid (60 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 8 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 40 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated which afforded 2,6-difluoro-3-isopropoxy-phenol (8.70 g, 100%) as a brown oil.

Source