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

Dimethyl phosphite (22.0 g, 0.2 mol) was added drop-wise to a solution of sodium methoxide (43.0 g) in methanol (100 ml) at 0°C. 2-Carboxybenzaldehyde (21.0 g, 0.1 mol) was then added portion-wise to the reaction mixture as a slurry in methanol (40 ml), with the temperature kept below 5°C. The resulting pale yellow solution was warmed to 20°C over 1 hour. Methanesulphonic acid (21.2 g, 0.22 mol) was added to the reaction drop-wise and the resulting white suspension was evaporated in vacuo. The white residue was quenched with water, extracted with chloroform (3 x 100 ml). The combined organic extracts was washed with water (2 x 100 ml), dried over MgS0Dimethyl phosphite (11 g, 0.1 mol) at 0 ° CAdd dropwise to a solution of sodium methoxide in methanol (100 ml).Then 2-carboxy benzaldehyde (10.5g, 0.05mol)Add to the reaction system, The entire process temperature is controlled below 5 °C.Thereafter, the mixture was heated to room temperature for 1 hour.Methanesulfonic acid (10.6 g, 0.11 mol) was added.The reaction solution was concentrated and washed with water and chloroform.The organic layers were combined and dried over anhydrous NaSO4.Concentrated to:3-oxo-1, 3-dihydroxy-isobenzofuran-1-phosphate dimethyl ester (16 g), The yield was 95percent.Dimethyl phosphite (22.0 g, 0.2 mol) was added drop-wise to a solution of sodium methoxide (43.0 g) in methanol (100 ml) at 0oC. 2- Carboxybenzaldehyde (21.0 g, 0.1 mol) was then added portion-wise to the reaction mixture as a slurry in methanol (40 ml), with the temperature kept below 5oC. The resulting pale yellow solution was warmed to 20oC over 1 hour. Methanesulphonic acid (21.2 g, 0.22 mol) was added to the reaction drop-wise and the resulting white suspension was evaporated in vacuo. The white residue was quenched with water and extracted into chloroform (3 x 100 ml). The combined organic extracts were washed with water (2 x 100 ml), dried over MGSO4, and evaporated in vacuo to yield (3-OXO-1, 3-dihydro-isobenzofuran-1-yl) phosphonic acid dimethyl ester as a white solid (32.0 g, 95 percent, 95 percent purity). This was then used without further purification in the next stage[0166] To a solution of sodium methoxide (5.4 M, 4.8 mL) in MeOH (20 mL) was added diethyl phosphite (3.31 g, 24 mmol) at 0 °C followed by addition of 2-formylbenzoic acid (3.0 g, 20 mmol) portion-wise over a period of 20 min. The resulting mixture was warmed up to rt and continued to stir for 2 h. Methanesulphonic acid (2.69 g, 28 mmol, 1.4 equiv.) was added to the above mixture over a period of 30 min. The reaction mixture was stirred for 30 min and concentrated to remove most of the MeOH. The residue was partitioned between DCM (100 mL) and water (50 mL). The aqueous layer was extracted DCM twice. The combined organic layer was dried over Nab.

Molecular Weight:242.16
XLogP3:0.4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:242.03441044
Monoisotopic Mass:242.03441044
Topological Polar Surface Area:61.8
Heavy Atom Count:16
Complexity:321
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes