Hydrochloric Acid → (3,5-Difluorophenyl)boronic acid

HRID 1071924Notes

Reaction equation

HRID 1071924 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.[B:15](OC)([O:18]C)[O:16]C.Cl>C(OCC)C>[F:14][C:9]1[CH:8]=[C:7]([B:15]([OH:18])[OH:16])[CH:12]=[C:11]([F:13])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 1363131-Bromo-3,5-difluorobenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 2734338(3,5-Difluorophenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

91.5 ml of tert-butyllithium are added at −78° C. to 20 g of 1-bromo-3,5-difluorobenzene in 300 ml of diethyl ether. The reaction mixture is stirred for 1 hour at −78° C. and 14.2 ml of trimethyl borate are then added. The reaction mixture is stirred for 1 hour at −78° C. and then for 12 hours at room temperature. 200 ml of aqueous 1 N hydrochloric acid solution are added. The resulting mixture is extracted with diethyl ether, the organic phase is washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulphate, and the solvents are evaporated off under reduced pressure. The residue is taken up in cyclohexane and the precipitate obtained is isolated by filtration.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at −78° C.
  2. waitfor 12 hours at room temperature
  3. extractionThe resulting mixture is extracted with diethyl ether
  4. washthe organic phase is washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents are evaporated off under reduced pressure
  7. customthe precipitate obtained
  8. customis isolated by filtration

Sources & evidence

ORD record
ord-c90d9b93a74c45e59840fd417fa97dae
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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