Thionyl Chloride → HCID 90408245, compound

HRID 2275412Notes

Reaction equation

HRID 2275412 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:22])=O>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:10]=1)[C:5]([Cl:22])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 467394923-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 90408245HCID 90408245, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
35 °C

Procedure

3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (700 mg, 2.67 mmol) was placed into 100 ml round bottom flask equipped with a stir bar. 3.0 ml of anhydrous chloroform was added to the flask followed by 2.0 ml of thionyl chloride and 1 drop of anhydrous DMF. The reaction mixture was stirred at 35° C. for 3 hours and then at room temperature overnight. LCMS of the sample after quenching a small amount with MeOH showed that no acid left. The solvent and excess thionyl chloride was removed under vacuum to give SKC-03-071. SKC-03-071 was used in the next step without further purification.

Workup

  1. customequipped with a stir bar
  2. customat room temperature
  3. customovernight
  4. customLCMS of the sample after quenching a small amount with MeOH
  5. waitleft
  6. customThe solvent and excess thionyl chloride was removed under vacuum
  7. customto give SKC-03-071
  8. customSKC-03-071 was used in the next step without further purification

Sources & evidence

ORD record
ord-fb7d125eff1c417d85b68e2002f7bcea
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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