Sodium Iodide → HCID 67296279, compound

HRID 2276852Notes

Reaction equation

HRID 2276852 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][B:9]([OH:11])[OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(#N)C>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][S:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][B:9]([OH:11])[OH:10])=[CH:6][CH:7]=1)[CH3:26]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 67296496HCID 67296496, compound

Product 1

HCID 67296279HCID 67296279, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Mercaptophenylboric acid 5.55 g (32.5 mmol) was dissolved in 80 mL of acetonitrile, followed by addition of potassium carbonate 6.73 g (48.7 mmol), sodium iodide 0.73 g (4.87 mmol) and ethyl bromoacetate 5.40 mL (8.13 g, 48.7 mmol), and the mixture was stirred for 18 hours at room temperature. The reaction solution was concentrated, followed by addition of water to the residue, and the residue was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was concentrated to give the title compound 7.80 g (yield 100%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionfollowed by addition of water to the residue
  3. extractionthe residue was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-2937c1e5c8fb4017bf00507aa83a0ac9
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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