Ammonium Chloride → 2-Fluoro-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester

HRID 1524945Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](I)=[CH:8][CH:7]=[CH:6][C:5]=1[F:11].C([Mg]Cl)(C)C.C(O[B:22]1[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]1)(C)C.[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)=[CH:8][CH:7]=[CH:6][C:5]=1[F:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 500 mL round-bottomed flask were added 2-fluoro-6-iodo-benzoic acid methyl ester (7.29, 26.0 mmol) and anhydrous THF (150 mL). This mixture was cooled to 0° C. and i-PrMgCl (13.7 mL, 2 M in THF, 27.3 mmol) was added dropwise. After 10 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.58 mL, 27.3 mmol) was added. The mixture was allowed to warm to room temperature, and after 30 min NH4Cl(aq) (150 mL, 13 wt % solution) was added. The layers were mixed and then separated, and the aqueous layer was extracted with 100 mL of MTBE. The combined organic layers were dried over Na2SO4, filtered, and concentrated to a final mass of 6.07 g (90% wt %, 75% yield). 1H NMR (400 MHz, CDCl3): 7.47-7.38 (m, 2H), 7.17-7.11 (m, 1H), 3.92 (s, 3H), 1.36 (s, 12H).

Workup

temperatureto warm to room temperature
additionThe layers were mixed
customseparated
extractionthe aqueous layer was extracted with 100 mL of MTBE
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated to a final mass of 6.07 g (90% wt %, 75% yield)

Sources & evidence

ORD record: ord-b96d0aeddfdd440ebea820fd73bb710c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079911B2

Reaction notes

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