Methanol → 2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester

HRID 336257Notes

Reaction equation

HRID 336257 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:24]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1)[C:5]([O:7][CH3:24])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 219239043-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterYield 89%

Procedure

To a suspension of 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (Synthech BC3558-001, 800 mg; 3.05 mmol; 1 eq.) in MeOH (16 mL) was added dropwise thionyl chloride (0.89 mL; 12.2 mmol; 4 eq.) and the reaction mixture was stirred at room temperature for 4 hours. The solvent evaporated in vacuo and the crude residue was diluted with Ethyl acetate (20 mL). The organic layer was washed with a sat. aq. NaHCO3 (5 mL), water (5 mL) and brine (5 mL), dried over magnesium sulfate and concentrated in vacuo to afford the title compound (751 mg, 89%) as a white solid.

Workup

  1. customThe solvent evaporated in vacuo
  2. additionthe crude residue was diluted with Ethyl acetate (20 mL)
  3. washThe organic layer was washed with a sat. aq. NaHCO3 (5 mL), water (5 mL) and brine (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f2a4b24482c4b4ca992d3c38a631697
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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