Potassium Carbonate → Ethoxymethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 38027

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.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:27][CH2:28]Cl)[CH3:26]>C(#N)C>[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][CH2:28][O:27][CH2:25][CH3:26])=[O:14])=[CH:11][CH:10]=2)[O:5]1

Participants

Conditions

Temperature: 65 °C

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.50 g, 2.02 mmol) was dissolved in 20 mls of dry acetonitrile. To this solution was added powdered potassium carbonate (0.42 g, 3.02 mmol) followed by chloromethyl ethyl ether (0.24 mls, 2.42 mmol). This mixture was warmed to 65° C. for 2 hours, then allowed to cool to room temperature, filtered and the filtrate concentrated to give ethoxymethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate as a solid (84%). This material was taken onto the next step without further purification.

Workup

temperatureto cool to room temperature
filtrationfiltered
concentrationthe filtrate concentrated

Sources & evidence

ORD record: ord-95a9a672e4e74bd9b0b2f18826c1a00a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524702B2

Linked notes

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