Hydrochloric Acid → 1-Chloro-4-fluoro-2-iodo-5-methoxyphenyl boronic acid

To 1-chloro-4-fluoro-2-iodo-5-methoxy-benzene (10.0 g, 34.9 mmol) in THF (70 mL) was cooled to −78° C. was added triisopropylborate (8.9 mL, 38.4 mmol) followed by dropwise addition of n-butyl lithium (24 mL of a 1.6 M solution in hexanes, 38.4 mL). The solution was stirred and allowed to warm to room temperature over night by dissipation of the dry ice/acetone bath. 1N HCl (50 mL0 and water (50 mL) were added and the solution stirred at room temperature for 1 h. The solution was extracted with ethyl acetate. The organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with 1:1 hexanes/diethyl ether and the solid collected by filtration to give 3.8 g (53%) of pure 1-chloro-4-fluoro-2-iodo-5-methoxyphenyl boronic acid: 1H NMR (400 MHz, CDCl3): δ 7.64 (d, J=11.7 Hz, 1H), 6.91 (d, J=7.3 Hz, 1H), 5.21 (br s, 2H), 3.90 (s, 3H).

1. stirringthe solution stirred at room temperature for 1 h
2. extractionThe solution was extracted with ethyl acetate
3. washThe organic layers were washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was triturated with 1:1 hexanes/diethyl ether
8. filtrationthe solid collected by filtration

ORD record

ord-9a9849e443944057ba38f2e830f5a9eb

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067658B2