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

HRID 2374113Notes

Reaction equation

HRID 2374113 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].C[O:15][B:16](OC)[O:17]C.Cl>C1COCC1>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[B:16]([OH:17])[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 97061,2-DifluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 2734333(2,3-Difluorophenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyllithium (2.5 M in hexanes, 88 ml, 0.219 mol) was added dropwise to a stirred, cooled (−78° C.) solution of difluorobenzene (25.0 g, 0.219 mol) in dry THF (400 ml) under a stream of dry nitrogen. The reaction mixture was maintained under these conditions for 2.5 h and then trimethylborate (45.5 g, 0.438 mol) was added dropwise to the reaction mixture and left overnight to reach room temperature. The reaction mixture was stirred for 1 h with 10% HCl (100 ml) at room temperature. The product was extracted into ether (2×200 ml) and the combined ethereal extracts were washed with water and dried (MgSO4), the solvent was removed under reduced pressure to give white crystals.

Workup

  1. temperatureThe reaction mixture was maintained under these conditions for 2.5 h
  2. customto reach room temperature
  3. extractionThe product was extracted into ether (2×200 ml)
  4. washthe combined ethereal extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customto give white crystals

Sources & evidence

ORD record
ord-f1a45954e17444b88fdda8dca97950b3
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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