4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → Methyl 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 2105042Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][C:14]1([CH3:21])[C:18]([CH3:20])([CH3:19])[O:17][BH:16][O:15]1>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:2]([B:16]2[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:21])([CH3:13])[O:15]2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 165 °C

Procedure

To a degassed mixture of methyl 2-iodo-6-methylbenzoate (220 mg, 0.9 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.16 mL, 1.1 mmol), TEA (0.4 mL, 2.7 mmol) in 2 mL dioxane was added Pd(PPh3)2Cl2 (20 mg, 0.03 mmol). The mixture was stirred at 165° C. for 10 min in a microwave oven. The mixture was diluted with EtOAc, washed with sat. NH4C1, H2O and brine, dried over (Na2SO4), filtered and concentrated. The crude product was purified by HPLC to afford 65 mg (35%) of Intermediate 296.1.

Workup

washwashed with sat. NH4C1, H2O and brine
dry with materialdried over (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by HPLC

Sources & evidence

ORD record: ord-3d07dc4c4e9b43b788d1ac8d51d814f7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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