Hydrochloric Acid → (4-{[3-(Methoxy)propyl]thio}phenyl)boronic acid

HRID 423535

Reaction equation

HRID 423535 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][O:15][CH3:16].C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.Cl>CC#N.O>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][S:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 5245511-Bromo-3-methoxypropaneHCID 44318944-Mercaptophenylboronic acid

Product 1

HCID 66673570(4-{[3-(Methoxy)propyl]thio}phenyl)boronic acidYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 1-bromo-3-methoxypropane (1.83 g, 11.7 mmol), K2CO3 (2.45 g, 17.5 mmol) and catalytic amount of Nal in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the mixture was extracted with CH2Cl2. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give a milky oil. Water was added to this oily residue, and the aqueous layer was acidified to pH about 2 with concentrated HCl. The mixture was let stand at ambient temperature overnight, and the off-white solid was collected via filtration and washed with water and hexane to give 1.07 g (81%) of (4-{[3-(methoxy)propyl]thio}phenyl)boronic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.98 (s, 2H), 7.68 (d, 2H, J=8.0 Hz), 7.22 (d, 2H, J=8.1 Hz), 3.38 (t, 2H, J=6.1 Hz), 3.19 (s, 3H), 2.98 (t, 2H, J=7.2 Hz), 1.85-1.70 (m, 2H); LRMS (ESI), m/z 225 (M−H).

Workup

  1. customAfter CH3CN was removed
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with CH2Cl2
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give a milky oil
  10. customat ambient temperature
  11. customovernight
  12. filtrationthe off-white solid was collected via filtration
  13. washwashed with water and hexane

Sources & evidence

ORD record
ord-2f37da26e75f485f94fa8f0c24b7ec00
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Linked notes

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