Water → HCID 66601935, compound

HRID 1615461Notes

Reaction equation

HRID 1615461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16]C(C)(C)C(C)(C)[O:13]2)=[CH:8][C:7]=1[O:21][CH3:22].I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]([OH:13])[OH:16])=[CH:8][C:7]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 666015592-(4-(3-Chlorophenoxy)-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 66601935HCID 66601935, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the compound (179.0 mg, 0.50 mmol) prepared in Example 9 in 10 mL acetone were added sodium periodate (318.0 mg, 1.49 mmol), ammonium acetate (84.0 mg, 1.09 mmol), and water (10 mL). The suspension was allowed to stir at room temperature for 18 hours. The acetone was removed under reduced pressure and the resulting aqueous layer was acidified with concentrated hydrochloric acid to pH 3. The resulting solid was collected and washed several times with water then dried under vacuum to obtain the title compound (106 mg) having the following physical data.

Workup

  1. customThe acetone was removed under reduced pressure
  2. customThe resulting solid was collected
  3. washwashed several times with water
  4. customthen dried under vacuum

Sources & evidence

ORD record
ord-1fdc39ed941949218669a5feee8b3a2a
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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