Trimethyl borate → HCID 56776693, compound

HRID 1624028Notes

Reaction equation

HRID 1624028 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[CH3:15].[B:16](OC)([O:19]C)[O:17]C>O1CCCC1>[F:14][C:10]1[C:11]([F:13])=[CH:12][C:7]([B:16]([OH:19])[OH:17])=[C:8]([CH3:15])[CH:9]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 448907851-Bromo-4,5-difluoro-2-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 56776693HCID 56776693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (4.6 mL, 11.5 mmol) is added to the mixture of 1-bromo-4,5-difluoro-2-methylbenzene (2.0 g, 9.6 mmol) and trimethyl borate (1.5 g, 14.5 mmol) in anhydrous tetrahydrofuran (30 mL), drop wise, at −78° C. over one hour, under an atmosphere of argon. The reaction mixture is stirred for another hour at the same temperature, quenched and acidified with 1 N HCl. The resulting mixture is extracted with ethyl acetate(3×). The combined organic layer is washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.

Workup

  1. customquenched
  2. extractionThe resulting mixture is extracted with ethyl acetate(3×)
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5f30ded778242a18f36e0ae85e096a5
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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