Water → (3-Cyano-5-fluorophenyl)boronic acid

HRID 2038372Notes

Reaction equation

HRID 2038372 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17]#[N:18])[CH:5]=[C:6]([B:8]2[O:12]C(C)(C)C(C)(C)[O:9]2)[CH:7]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[C:17]([C:4]1[CH:5]=[C:6]([B:8]([OH:12])[OH:9])[CH:7]=[C:2]([F:1])[CH:3]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 467381943-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.00 g (4.05 mmol) of the compound from Example 21A is provided in 40 ml of acetone, 2.60 g (12.1 mmol) of sodium periodate, 0.70 g (9.11 mmol) of ammonium acetate and 40 ml of water are added and the mixture is stirred at room temperature overnight. The mixture is subsequently concentrated, a 2N aqueous sodium hydroxide solution is added to the residue and the precipitate that remains is filtered off with suction. Using a concentrated aqueous hydrogen chloride solution, the solution is adjusted to pH 3 and cooled to 0° C. The precipitate formed is collected by suction filtration, washed with water and dried under high vacuum. 384 mg (58% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is subsequently concentrated
  2. additiona 2N aqueous sodium hydroxide solution is added to the residue
  3. filtrationthe precipitate that remains is filtered off with suction
  4. temperaturecooled to 0° C
  5. customThe precipitate formed
  6. filtrationis collected by suction filtration
  7. washwashed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-a4cd4ae3be334e23935f8caef30cdd6f
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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