ChemicalBook CAS DataBase List 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid synthesis

7synthesis methods

Product Name:3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid
CAS Number:61260-15-9
Molecular formula:C10H11O5P
Molecular Weight:242.17

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development. It was prepared from Dimethyl phosphite and o-carboxybenzaldehyde by stirring in methanol for 6 h at room temperature.

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3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid

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Yield:61260-15-9 96%

Reaction Conditions:

Stage #1: dimethyl phosphonate;o-carboxybenzaldehydewith natrium in methanol at 0 - 20; for 6 h;
Stage #2: with Eaton′s Reagent in methanol; for 0.5 h;

Steps:

1.2 Dimethyl (3-oxo-l,3,-dihydroisobenzofuran-l-yl)phosphonate

Dimethylphosphite (0.92 mL, 10.0 mmol) was added dropwise to a solution of sodium (0.58 g, 10.8 mmol) in MeOH (15 mL) at 0°C. To the solution, 2-carboxybenzaldehyde (1.00 g, 6.66 mmol) was added portionwise while stirring. The mixture was gradually warmed to room temperature and stirred for 6 hours. Methanesulfonic acid (0.77 mL, 11.9 mmol) was added dropwise and the mixture was stirred for another 30 minutes. The solution was concentrated in vacuo to produce a white solid, to which water was added (30 mL) and the crude product was extracted into DCM (3 x 30 mL). The organic layer was washed with water (2 x 30 mL), dried with MgS0₄ and filtered. The filtrate was concentrated in vacuo and washed with EbO (3 x 20 mL), affording Dimethyl-(3-oxo-l,3-dihydrobenzofuran-l- yl)phosphonate (1.54 g, 96%) as a white solid. *H NMR (400 MHz, CD₃OD) d = 7.94 (d, J = 7.5 Hz 1H), 7.83 (t, J = 7.5 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.68 (t, J = 7.5 Hz, 1H), 6.10 (d, J = 10.8, 1H), 3.91 (d, J = 10.8 Hz, 3H), 3.72 (d, J - 10.8 Hz, 3H). Data is in accordance with known literature; Mp: 90 - 92°C (Menear, K.A., et al. 4-[3-(4-cyclopropanecarbonylpiperazine-l-carbonyl)-4-fluorobenzyl]-2H- phthalazin- l-one: a novel bioavailable inhibitor of poly(ADP-ribose) polymerase- 1. J Med Chem 51, 6581-6591, 2008).

References:

WO2019/186135,2019,A1 Location in patent:Page/Page column 62-63