2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic Acid → Tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

HRID 2364651Notes

Reaction equation

HRID 2364651 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)[O:3]1.C(N/C(=N/C(C)C)/O[C:26]([CH3:29])([CH3:28])[CH3:27])(C)C>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:17])=[CH:11][CH:10]=2)[O:5]1

Participants

4

Reactant 2

HCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic AcidHCID 178457538HCID 178457538, compound

Product 1

HCID 57992009Tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetateYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (0.250 g, 0.954 mmol) was dissolved in 10 mls of dry THF. To this solution was added (Z)-tert-butyl N,N′-diisopropylcarbamimidate (3.82 g, 19.08 mmol) and the mixture was allowed to stir at room temperature for 16 hours. The mixture was then filtered, filtrate concentrated under reduced pressure and purified by a 50 g Snap cartridge (Biotage, 10% EtOAc/Hexanes) to give 280 mgs (92%) of tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate as a thick oil.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationfiltrate concentrated under reduced pressure
  3. custompurified by a 50 g Snap cartridge (Biotage, 10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ccc35857a2a2490286eef08eaa0bfce6
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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