Thionyl Chloride → 2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride

HRID 2275416Notes

Reaction equation

HRID 2275416 reaction equation
[CH3:1][C:2]1[C:10]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:22])=O>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:10]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:22])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 218867032-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 904078612-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chlorideYield 70.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (1.2 g, 46.0 mmol) was placed into 40 ml scintillation vial equipped with a small stir bar. 10.0 ml of anhydrous chloroform was added following by 1.8 ml of thionyl chloride and 2 drops of anhydrous DMF. After 3 hours, the solvent and excess thionyl chloride were evaporated under vacuum. The brown residue was treated with 40 ml of hexane, filtered, and concentrated to give 985 mg (Yield=70.5%) of the product as a greenish oil. 1H NMR (CDCl3, 400 MHz) δ 8.15 (d, 1H), 7.95 (d, 1H), 7.3 (t, 1H), 2.75 (s, 3H), 1.4 (s, 12H). The reaction was run several times and the yield was ranging from 60 to 99%.

Workup

  1. customvial equipped with a small stir bar
  2. customthe solvent and excess thionyl chloride were evaporated under vacuum
  3. additionThe brown residue was treated with 40 ml of hexane
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a2927a3166f494aa142ce44a80e753e
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

Loading…