Hydrochloric Acid → 4-(Trifluoromethoxy)phenylboronic acid

HRID 2306090Notes

Reaction equation

HRID 2306090 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C.Cl>C1COCC1.BrC1C=CC(OC(F)(F)F)=CC=1>[F:11][C:10]([F:13])([F:12])[O:9][C:6]1[CH:7]=[CH:8][C:3]([B:14]([OH:19])[OH:15])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224Magnesium

Product 1

HCID 27343864-(Trifluoromethoxy)phenylboronic acid

Reagents, catalysts & solvents 2

HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of magnesium (3.25 g) in THF (25 mL) at room temperature was treated with several drops of 1-bromo-4-(trifluoromethoxy)benzene, stirred for several minutes, treated with THF (100 mL), treated with 1-bromo-4-(trifluoromethoxy)benzene (30.8 g), heated to reflux, stirred for 16 hours, treated with triisopropyl borate (34 mL) over 10 minutes, stirred for 1 hour, cooled to 0° C., treated with 6M HCl (50 mL), stirred for 45 minutes, and extracted with isopropyl acetate. The extract was washed with brine, filtered, and concentrated to provide 21.5 g of 4-(trifluoromethoxy)phenylboronic acid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for 16 hours
  4. stirringstirred for 1 hour
  5. stirringstirred for 45 minutes
  6. extractionextracted with isopropyl acetate
  7. washThe extract was washed with brine
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a4c54f3b2a644773b452cfc47e34a11a
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

Loading…