4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → Tert-butyl 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 2105086Notes

Reaction equation

[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11](I)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][BH:19][O:18]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>[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([B:19]2[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:24])([CH3:16])[O:18]2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

Conditions

Temperature: 165 °C

Procedure

To a degassed mixture of tert-butyl 2-fluoro-6-iodobenzoate (161 mg, 0.5 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.1 mL, 0.6 mmol) and TEA (0.25 mL, 1.5 mmol) in 2 mL dioxane, was added Pd(PPh3)2Cl2 (7 mg, 0.01 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 flash chromatography (0-10% EtOAc/hexanes gradient) to afford 50 mg (45%) of Intermediate 436.2.

Workup

washwashed with sat. NH4C1, H2O and brine
dry with materialdried over (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography (0-10% EtOAc/hexanes gradient)

Sources & evidence

ORD record: ord-30f6fec4913f464482235657f5686e4f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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