Hydrogen Peroxide → Phenol, 5-bromo-2-fluoro-

A solution of 5-bromo-2-fluorobenzeneboronic acid (25 g, 114 mmol) in tetrahydrofuran was treated with hydrogen peroxide (7.8 ml of a 35 wt % solution in water) then with sodium hydroxide (1.4 ml of a 4N solution in water). A mild exotherm caused the internal temperature to reach 40° C. This mixture was left to stir at ambient temperature for 14 h then treated with manganese dioxide (200 mg) and stirring was continued for 90 min before filtering the reaction (GF/A filter paper). The filtrate was concentrated on a rotary evaporator and the residue partitioned between ether (400 ml) and water. The organics were washed with more water and brine, and dried over anhydrous magnesium sulphate. Filtration and evaporation to dryness afforded 5-bromo-2-fluorophenol (19.7 g, 90%) as a colourless liquid: δH (400 MHz, d6-DMSO) 6.93-6.97 (1H, m), 7.09-7.14 (2H, m), 10.36 (1H, br).

1. customto reach 40° C
2. waitThis mixture was left
3. stirringstirring
4. waitwas continued for 90 min
5. filtrationbefore filtering
6. customthe reaction (GF/A filter paper)
7. concentrationThe filtrate was concentrated on a rotary evaporator
8. customthe residue partitioned between ether (400 ml) and water
9. washThe organics were washed with more water and brine
10. dry with materialdried over anhydrous magnesium sulphate
11. filtrationFiltration and evaporation to dryness

ORD record

ord-98506153afa7442da2d0fc39837b1b2e

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279580B2