Dimethyl Sulfoxide → (3-Cyclopropoxyphenyl)boronic acid

HRID 42010Notes

Reaction equation

HRID 42010 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]2[CH2:11][CH2:10]2)[CH:3]=1.CC1(C)C(C)(C)[O:16][B:15](B2OC(C)(C)C(C)(C)O2)[O:14]1.C(Cl)Cl.CS(C)=O>C(OCC)(=O)C>[CH:9]1([O:8][C:4]2[CH:3]=[C:2]([B:15]([OH:16])[OH:14])[CH:7]=[CH:6][CH:5]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 2733548Bis(pinacolato)diboraneHCID 574169511-Bromo-3-cyclopropoxybenzene

Product 1

HCID 67394331(3-Cyclopropoxyphenyl)boronic acidYield 37.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-3-cyclopropoxybenzene (1.36 mmol, 0.289 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (2.11 mmol, 0.321 mmol), PdCl2dppf.DCM (0.14 mmol, 0.112 g), KAcO (6.11 mmol, 0.600 g) in a DMSO (3 ml) was heated at 130° C. for 45 minutes, under argon atmosphere in a microwave oven. Ethyl acetate was added and filtered through celite. The organic phase was washed with water and evaporated. The crude mixture was purified by reverse phase using a water/AcN/MeOH system gradient affording 0.090 g (yield 23%) of the expected product.

Workup

  1. filtrationfiltered through celite
  2. washThe organic phase was washed with water
  3. customevaporated
  4. customThe crude mixture was purified by reverse phase

Sources & evidence

ORD record
ord-94d740c927e444fe9813916260d9a07a
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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