Lithium Hydroxide → 3-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}benzoic acid

HRID 928673Notes

Reaction equation

HRID 928673 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.Br[CH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24]C)=[O:23].C(=O)([O-])[O-].[K+].[K+].[OH-].[Li+]>C(OCC)(=O)C.O.CO.CN(C=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])=[CH:11][CH:10]=2)[O:5]1

Participants

9

Reactant 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 903844063-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}benzoic acid

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DMF (125 mL) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (8.46 g, 38 mmol), methyl 3-(bromomethyl)benzoate (8.8 g, 38 mmol), and potassium carbonate (10.6 g, 77 mmol), and stirred at room temperature overnight. The resultant was diluted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and to the resulting residue, methanol (150 mL), water (30 mL), and lithium hydroxide (4.8 g, 114 mmol) were added, and stirred at room temperature overnight. After the solvent was distilled away under reduced pressure, the resultant was diluted with ethyl acetate, then washed with 1 N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, the solid was collected by filtration.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. stirringstirred at room temperature overnight
  5. distillationAfter the solvent was distilled away under reduced pressure
  6. additionthe resultant was diluted with ethyl acetate
  7. washwashed with 1 N hydrochloric acid and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled away under reduced pressure
  10. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-eb1b9ea2986641db835f576bdba1618f
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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