Hydrochloric Acid → 4-(1-(Tert-butyldimethylsilyloxy)propan-2-yl)phenylboronic acid

HRID 735689Notes

Reaction equation

HRID 735689 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Li]CCCC.[B:24](OC)([O:27]C)[O:25]C.Cl>>[Si:11]([O:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([B:24]([OH:27])[OH:25])=[CH:3][CH:4]=1)[CH3:18])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 57842594(2-(4-Bromophenyl)propoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 578427824-(1-(Tert-butyldimethylsilyloxy)propan-2-yl)phenylboronic acidYield 41.9%

Conditions

Temperature
-78 °C

Procedure

To a solution of 73C (100 mg in 2 mL dry THF, 0.3 mmol) at −78° C. was added n-BuLi (1.6 M, 0.2 mL, 0.32 mmol), followed by B(OMe)3 (0.1 mL, 0.9 mmol). The solution was stirred at −78° C. for 2 h. 1N HCl (4 mL) was added, and stirred 30 min. The mixture was extracted with EtOAc (3×20 mL). The organic layer washed by brine, dried (Na2SO4). Purification through ISCO (0-80% EtOAc in hexanes) gives 73D (37 mg, 40%). 1H NMR (400 MHz, Chloroform-d) δ ppm −0.03 (d, J=3.52 Hz, 6 H) 0.84-0.89 (m, 9 H) 1.33 (d, J=7.03 Hz, 3H) 2.92-3.06 (m, 1 H) 3.62-3.79 (m, 2 H) 7.36 (d, J=7.91 Hz, 2 H) 8.16 (d, J=7.91 Hz, 2 H)

Workup

  1. stirringstirred 30 min
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. washThe organic layer washed by brine
  4. dry with materialdried (Na2SO4)
  5. customPurification through ISCO (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b5d900e93beb4859a25fc494c0c1cbd6
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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