Sodium Iodide → HCID 86702801, compound

HRID 1425936Notes

Reaction equation

HRID 1425936 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH2:11]CS([O-])(=O)=O)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.[Na+].[I-].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.CCOC(C)=O>[N:19]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)=[N+:20]=[N-:21]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 86702802HCID 86702802, compound

Product 1

HCID 86702801HCID 86702801, compoundYield 131%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylmethanesulfonate (CIX) (0.48 g, 1.98 mmol) in DMF (20 mL) was added NaI (0.06 g, 0.40 mmol) and NaN3 (0.15 g, 2.38 mmol). The mixture was stirred at 60° C. overnight. The reaction mixture was diluted with EtOAc, washed with 10% aqueous Na2S2O3, brine, dried over anhydrous MgSO4, and concentrated under vacuum to give 6-(azidomethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CX) (0.49 g, impure). The crude product was used without further purification for step 7.

Workup

  1. washwashed with 10% aqueous Na2S2O3, brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-536de4e2614d45109363b4471d06cfa8
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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