Dichloromethane → (4-Methoxy-2-nitrophenyl)boronic acid

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (5 g, 17.9 mmol) in THF (50 mL) cooled to −60° C. was added phenylmagnesium bromide (10.4 mL, 25 wt %, 19.7 mmol) which gave a dark red solution. Trimethylborate (2.4 mL, 21.5 mmol) was then added dropwise. After 30 min, the reaction was quenched with 1 N HCl (40 mL) and extracted with ether. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo to give a dark brown oil which was tritrated with DCM to yield (4-methoxy-2-nitrophenyl)boronic acid as grey solid. A portion of this material (1.57 g, 8 mmol) was then taken up in DME (1 mL) and 1-bromo-4-iodo-2-methoxybenzene (C1, step 1) (2.5 g, 8 mmol), CsF (2.73 g, 18 mmol), and tetrakistriphenylphosphine palladium (0.92 g, 0.8 mmol) under nitrogen. The mixture was then heated to 100° C. for 18 h. The mixture was then extracted with water and EtOAc. The organic layer was then dried over Na2SO4 and the solvent was removed in vacuo. The crude material was then purified on silica (gradient elution, 3-50% EtOAc/hexanes) to yield the title compound as a yellow solid.

1. customgave a dark red solution
2. customthe reaction was quenched with 1 N HCl (40 mL)
3. extractionextracted with ether
4. dry with materialThe organic layer was then dried over Na2SO4
5. customthe solvent was removed in vacuo
6. customto give a dark brown oil which

ORD record

ord-25475b9480774b949cae8f02fd8b9465

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927569B2