Hydrochloric Acid → 4-Fluorophenylboronic acid

HRID 964482Notes

Reaction equation

HRID 964482 reaction equation
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.[F:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.CCOCC.Cl>C1COCC1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([B:1]([OH:6])[OH:2])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21531Triisopropyl borateHCID 178418676HCID 178418676, compound

Product 1

HCID 2856454-Fluorophenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of triisopropyl borate (4.6 mL, 20 mmol) in THF (1 mL) at -78° C. under nitrogen was added 4-fluorophenylmagnesium bromide (2M solution in diethylether, 10 mL) dropwise. The mixture was allowed to warm to room temperature. Ether (50 mL) was added, followed by 10% HCl (50 mL). The ether layer was then washed with H2O (25 mL) and brine (25 mL). The dried (MgSO4) ether layer was concentrated to dryness. The residue was triturated with hexanes to provide an off-white solid which was filtered and dried under vacuum to afford 1.38 g of 4-fluorophenyl boronic acid.

Workup

  1. washThe ether layer was then washed with H2O (25 mL) and brine (25 mL)
  2. dry with materialThe dried (MgSO4) ether layer
  3. concentrationwas concentrated to dryness
  4. customThe residue was triturated with hexanes
  5. customto provide an off-white solid which
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8b030c9693db43a4bd4781a7c9ca915a
Source dataset
uspto-grants-1998_06
Patent number
US05770180

Reaction notes

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