Trimethyl borate → [5-Tert-butyl-2-(methoxymethoxy)phenyl]boronic acid

HRID 1480626Notes

Reaction equation

HRID 1480626 reaction equation
C([Li])(C)(C)C.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].[B:20](OC)([O:23]C)[O:21]C>CCCCC>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[C:12]([B:20]([OH:23])[OH:21])[CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 150654751-(Tert-butyl)-4-(methoxymethoxy)benzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 86718588[5-Tert-butyl-2-(methoxymethoxy)phenyl]boronic acidYield 110.1%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Following a procedure by Ronald, R. C. et al (J. Org. Chem., 1980, 40, 2224-2229) a 1.7 molar solution of tert-butyl lithium in pentane (6.70 mL, 11.3 mmol) was added to a solution of 1-(tert-butyl)-4-(methoxymethoxy)benzene (2.00 g, 10.3 mmol, Kovacs, M. S. et al J. Chem. Soc. Dalton, 2001, 3015-3024) in pentane (40 mL) under a nitrogen atmosphere at 0° C. A solid precipitated and the pentane was evaporated under a steady stream of nitrogen gas. To this remaining solid was added tetrahydrofuran (50 mL) and the solution was cooled to −78° C. Trimethyl borate (1.70 mL, 15.5 mmol) was added slowly and the solution was stirred at −78° C. under nitrogen gas for 30 minutes. Thin layer chromatography showed consumption of the starting material and water (10 mL) was added and the solution was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide solution. The organic phase was separated and dried with sodium sulfate, filtered and concentrated under reduced pressure to give 2.70 g of crude (5-(tert-butyl)-2-(methoxymethoxy)phenyl)boronic acid which was used without further purification.

Workup

  1. customA solid precipitated
  2. customthe pentane was evaporated under a steady stream of nitrogen gas
  3. additionTo this remaining solid was added tetrahydrofuran (50 mL)
  4. customconsumption of the starting material and water (10 mL)
  5. additionwas added
  6. customthe solution was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide solution
  7. customThe organic phase was separated
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12257cc04c0b456c9f5ef0b3336f18a5
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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