Methanol → Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 1531389Notes

Reaction equation

HRID 1531389 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[O:3]1.[CH3:19]O>>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:18])([CH3:1])[O:3][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:19])=[O:14])=[CH:11][CH:10]=2)[O:5]1

Participants

3

Reactant 2

HCID 887MethanolHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 83%

Procedure

50 g (200 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid and 1,22 g (10 mmol) of N,N-dimethylpyridine are dissolved in 200 ml of methanol and refluxed for 5 hours. Removal of 150 ml of methanol by distillation gives 43.4 g (165 mmol, 83%) of product.

Workup

  1. temperaturerefluxed for 5 hours
  2. customRemoval of 150 ml of methanol
  3. distillationby distillation

Sources & evidence

ORD record
ord-e21e1a5ed65d449a85c90f2af27906e9
Source dataset
uspto-grants-2001_03
Patent number
US06197967B1

Reaction notes

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