Trimethyl borate → HCID 66692124, compound

HRID 1773647Notes

Reaction equation

HRID 1773647 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:3]=1[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].C([Li])CCC.[B:26](OC)([O:29]C)[O:27]C.[Cl-].[NH4+]>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:2]([B:26]([OH:29])[OH:27])=[C:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 66691631HCID 66691631, compoundHCID 178418339Butyllithium

Product 1

HCID 66692124HCID 66692124, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 6.00 g (16.6 mmol) [(2-bromo-5-fluorobenzyl)oxy](triisopropyl)silane which was prepared according to intermediate example 299c in 60 mL tetrahydrofuran were added 7.31 mL n-butyllithium (2.5M in hexane) at −78° C. After 20 minutes of stirring 5.58 mL trimethyl borate were added and stirring was continued for additional 60 minutes. The mixture was allowed to warm to 23° C., poured into a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 3.16 g (58%) of the title compound.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and removal of the solvent the residue
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-1483295540d04e1e9b9efd3362b2f893
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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