Trifluoroacetic acid → 6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037051Notes

Reaction equation

HRID 1037051 reaction equation
C(O)(C(F)(F)F)=O.O[C:9]([C:12]1[CH:13]=[CH:14][C:15]2[C:19]([CH3:21])([CH3:20])[O:18][B:17]([OH:22])[C:16]=2[CH:23]=1)([CH3:11])[CH3:10].[N-:24]=[N+:25]=[N-:26].[Na+]>C(Cl)(Cl)Cl>[N:24]([C:9]([C:12]1[CH:13]=[CH:14][C:15]2[C:19]([CH3:21])([CH3:20])[O:18][B:17]([OH:22])[C:16]=2[CH:23]=1)([CH3:11])[CH3:10])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 866854966-(2-hydroxypropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 866854956-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-olYield 102%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of TFA (200 μL, 2 mmol) in chloroform (3 mL) was added slowly to a mixture of 6-(2-hydroxypropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol (88 mg, 0.4 mmol) and sodium azide (80 mg, 1.2 mmol) in chloroform (7 mL) at −5° C. to 0° C. The cooling bath was removed and the mixture was stirred at rt overnight. Concentrated ammonium hydroxide was added until pH was basic (moist PH paper). DCM (50 mL) was added and the organic layer was washed with brine:water (1:1), dried over Na2SO4, filtered and concentrated to give the crude product 6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol (100 mg) as colorless oil. It was used without further purification in the next step.

Workup

  1. customThe cooling bath was removed
  2. additionConcentrated ammonium hydroxide was added until pH
  3. additionDCM (50 mL) was added
  4. washthe organic layer was washed with brine:water (1:1)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2130401305f74ed48c61154281de903d
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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