Potassium Carbonate → {4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acid

HRID 423533Notes

Reaction equation

HRID 423533 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][C:13]([NH2:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:15][C:13](=[O:14])[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 44318944-Mercaptophenylboronic acid

Product 1

HCID 66673418{4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acidYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 2-bromoacetamide (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.6 g (49%) of {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid as a white solid. The boronic acid was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 2H), 7.68 (d, 2H, J=8.2 Hz), 7.55 (bs, 1H), 7.24 (d, 2H, J=8.2 Hz), 7.15 (bs, 1H), 3.61 (s, 2H); LRMS (APCI), m/z 210 (M−H).

Workup

  1. customAfter CH3CN was removed
  2. additionwater was added to the residue
  3. filtrationthe solid was collected via filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-cc96d83cf8c44c2f95e2db6ce75b7cac
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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