HCID 68281454, compound → HCID 68281360, compound

HRID 1425943Notes

Reaction equation

HRID 1425943 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([F:17])([F:16])[F:15])[C:7]2[CH2:11][O:10][B:9]([OH:12])[C:8]=2[CH:13]=1)([O-])=O.C([O-])(O)=O.[Na+].CCOC(C)=O>CO.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([F:16])([F:17])[F:15])[C:7]2[CH2:11][O:10][B:9]([OH:12])[C:8]=2[CH:13]=1

Participants

5

Reactant 2

HCID 68281454HCID 68281454, compoundHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 68281360HCID 68281360, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitro-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXXI) (0.95 g, 3.83 mmol) in MeOH/2M HCl mixture (1:1) (129 mL) was added Zn (dust) (2.5 g, 38.31 nmol). The reaction mixture was stirred at room temperature for 3 hours before it was slowly neutralized by a solution of saturated aq. NaHCO3/EtOAc (1:1, 100 mL/100 mL). Then the reaction mixture was filtered through Celite and washed with EtOAc. The organic layer was washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and evaporated to dryness to yield 6-amino-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXXII) as a slightly brown crystalline solid (700 mg, 3.22 mmol, 84% yield). ESIMS found for C8H7BF3NO2 m/z 216.4 (M−H).

Workup

  1. filtrationThen the reaction mixture was filtered through Celite
  2. washwashed with EtOAc
  3. washThe organic layer was washed with 5% NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8f52d2b005e644988ffe7e50934528db
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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