Diethyl chlorophosphate → HCID 24807582, compound

Temperature

-78 °C

To a 200 mL round-bottom flask equipped with a magnetic stir-bar was added phosphorochloridic acid diethyl ester (17.25 mL, 120 mmole) and THF (200 mL). The mixture was cooled to −78° C. and a solution of cyclopropylmagnesium bromide (200 mL, 0.5 M in THF, 100 mmol) was added dropwise over 30 minutes using an addition funnel. The reaction was allowed to slowly warm to room temperature overnight. The resulting clear reaction mixture was poured into saturated NH4Cl (200 mL) and partitioned. The product was extracted from the aqueous layer with diethyl ether (1×100 mL). The organic fractions were combined, dried over sodium sulfate, and concentrated in vacuo. The resulting yellow oil was further purified by vacuum distillation (65-75° C. at 500 mTorr) to provide cyclopropylphosphonic acid diethyl ester (9.025 g, 51%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 4.11-4.03 (m, 4H), 1.32-1.29 (m, 6H), 0.90-0.77 (m, 5H); 13C NMR (100 MHz, CDCl3) δ ppm 61.7 (d, J=5.3 Hz), 16.4 (d, J=6.1 Hz), 3.3 (d, J=196.3 Hz), 3.0 (d, J=4.6 Hz).

1. customTo a 200 mL round-bottom flask equipped with a magnetic stir-bar
2. temperatureto slowly warm to room temperature overnight
3. custompartitioned
4. extractionThe product was extracted from the aqueous layer with diethyl ether (1×100 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. distillationThe resulting yellow oil was further purified by vacuum distillation (65-75° C. at 500 mTorr)

ORD record

ord-8eff5b5bd2d249d489d2bad5e96262ef

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625880B2