Potassium Carbonate → 2-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1469357Notes

Reaction equation

HRID 1469357 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([B:14]2[O:22][C:19]([CH3:21])([CH3:20])[C:16]([CH3:18])([CH3:17])[O:15]2)[CH:11]=[CH:12][CH:13]=1.[CH3:23][O:24][CH2:25][CH2:26]Br>CN(C=O)C>[CH3:23][O:24][CH2:25][CH2:26][O:7][C:8]1[CH:9]=[C:10]([B:14]2[O:22][C:19]([CH3:21])([CH3:20])[C:16]([CH3:17])([CH3:18])[O:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 595587402-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (1.88 g, 13.65 mmol) was added to a solution of −3-hydroxyphenylboronic acid pinacol ester (Apollo, 1.0 g, 4.55 mmol) in DMF (10 mL). 2-Bromoethyl methyl ether (0.41 mL, 5.46 mmol) was added and the reaction mixture was heated to 100° C. for 1 hr. The reaction mixture was allowed to cool and then partitioned between ethyl acetate (50 mL), and water (150 mL). The phases were separated and the organic phase was washed with brine (150 mL), dried over anhydrous sodium sulphate, filtered and the filtrate solvents removed in vacuo, to afford the title product as a light-brown oil (1.1 g) which was used without further purification.

Workup

  1. temperatureto cool
  2. custompartitioned between ethyl acetate (50 mL), and water (150 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with brine (150 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe filtrate solvents removed in vacuo

Sources & evidence

ORD record
ord-5290bbc5ba4248f5b05b448c9ecfa57e
Source dataset
uspto-grants-2015_04
Patent number
US09006269B2

Reaction notes

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