Triisopropyl borate → (4-(Morpholin-4-yl)phenyl)boronic acid

HRID 1992317Notes

Reaction equation

HRID 1992317 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:19]([OH:24])[OH:20])=[CH:3][CH:4]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 116228514-(4-Bromophenyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in step 1 (0.3 g) in THF (15 mL) was added n-BuLi (0.74 mL, 2 M in pentane) at 78° C. After 1 h triisopropyl borate (0.86 mL) was added at −78° C. The solution was warmed up slowly from −78° C. to room temperature and was stirred overnight. The solution was added to aqueous NH4Cl, a white precipitate formed, and EtOAc was added. The organic solution was separated, concentrated and co-evaporated with toluene. The residue washed twice with THF and filtered. The filtrate was concentrated and dried under high vacuum to give 0.25 g of light yellow precipitate. LC/MS m/z 208 (M+H)+.

Workup

  1. temperatureThe solution was warmed up slowly from −78° C. to room temperature
  2. customa white precipitate formed
  3. customThe organic solution was separated
  4. concentrationconcentrated and co-evaporated with toluene
  5. washThe residue washed twice with THF
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-0ef122813de144669c6cda1474f54465
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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