Water → {4-[(Morpholin-4-yl)methyl]phenyl}boronic acid

HRID 2206189Notes

Reaction equation

HRID 2206189 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.O>C(#N)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27355934-(Bromomethyl)phenylboronic acid

Product 1

HCID 10998582{4-[(Morpholin-4-yl)methyl]phenyl}boronic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (4-(bromomethyl)phenyl)boronic acid (500 mg) and potassium carbonate (643 mg) in acetonitrile (10 mL) was added morpholine (0.304 mL), and the mixture was stirred at room temperature for 60 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed with diisopropyl ether and ethyl acetate to give the title compound (449 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained solid was washed with diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-0441280d34ea42feb9d3ea29622c73a8
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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