Hydrochloric Acid → (2,3-Difluorophenyl)boronic acid

HRID 2292425Notes

Reaction equation

HRID 2292425 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C.Cl>C1COCC1>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[B:14]([OH:19])[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97061,2-DifluorobenzeneHCID 21531Triisopropyl borateHCID 178418339Butyllithium

Product 1

HCID 2734333(2,3-Difluorophenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllitium (30 cm3, 10M in hexanes, 0.3 mol) was added dropwise to a stirred, cooled (-78° C.) solution of 1,2-difluorobenzene (34.5 g, 0.3 mol) in dry THF (350 cm3) under a atmosphere of dry nitrogen. The reaction mixture was stirred (2.5 h) then a previously cooled (-78° C.) solution of triisopropyl borate (113 g, 0.6 mol) in dry THF (200 cm3) added dropwise at -78° C. The reaction mixture was allowed to warm to room temperature overnight then stirred (1 h) with hydrochloric acid (10%, 300 cm3). The product was extracted into diethyl ether (2×300 cm3), and the combined extracts washed with water and dried (MgSO4). The solvent was removed in vacuo to yield colourless crystals.

Workup

  1. additionadded dropwise at -78° C
  2. extractionThe product was extracted into diethyl ether (2×300 cm3)
  3. washthe combined extracts washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto yield colourless crystals

Sources & evidence

ORD record
ord-a023fd00b6aa43d6b15355a1f38ef8db
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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