Water → Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate

HRID 30760

Reaction equation

Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C:9]1([CH3:23])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[O:10]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:14][C:13]1([CH3:15])[C:9]([CH3:8])([CH3:23])[O:10][B:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:18][CH:17]=2)[O:12]1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl bromoacetate (0.60 mL) was added to a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.0 g) and potassium carbonate (0.94 g) in N,N-dimethylformamide (5 mL), and the mixture was stirred overnight at 80° C. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1) to afford the title compound (1.33 g).

Workup

customThe organic layer was separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-50ce0f1ccacb469eb7d8d8c9ddffe9fa
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423185B2

Linked notes

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