4-Chlorobenzenesulfonyl chloride → HCID 68238947, compound

A solution of 7-nitro-3,4-dihydro-benzo[c][1,2]oxaborinin-1-ol (694.6 mg, 3.6 mmol) in THF (70 mL) was passed through H-cube equipped with a 10% Pd/C cartridge. The collected light yellow solution was treated with Et3N (0.6 mL, 4.3 mmol, 1.2 eq.) and divided evenly into 12 portions. To a portion of the solution was added 4-chloro-benzenesulfonyl chloride (63.3 mg, 0.29 mmol). The resulting mixture was stirred at room temperature overnight. The reaction solution was diluted with EtOAc (20 mL), washed with 1N HCl (10 mL), H2O (10 mL), brine (10 mL) and concentrated under reduced pressure. The residue was dissolved in minimal amount of THF and then titrated with heptanes to vive a white suspension. The precipitate was collected by filtration, washed with heptanes to give the title compound as a white solid. LCMS (M/Z): 338 (M+H); 1H NMR (DMSO-d6) δ: 10.17 (s, 1H), 8.39 (s, 1H), 7.65-7.70 (m, 2H), 7.56-7.61 (m, 2H), 7.32 (d, J=1.8 Hz, 1H), 7.02-7.08 (m, 2H), 3.96 (t, J=5.9 Hz, 2H), 2.72 (t, J=5.9 Hz, 2H).

1. customThe collected light yellow solution
2. washwashed with 1N HCl (10 mL), H2O (10 mL), brine (10 mL)
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in minimal amount of THF
5. filtrationThe precipitate was collected by filtration
6. washwashed with heptanes

ORD record

ord-af374a5678ad4f8d8f614e8008aaee2d

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623911B2