Diboron → HCID 56976335, compound

4-(Diethyl phosphonomethyl)benzoic acid (66 mmol) was suspended in anhydrous THF (75 mL) under a nitrogen atmosphere. The reaction was cooled in an ice bath while diborane 1M in THF (72.6 mmol ) was added dropwise to the acid. Once the addition was complete the reaction was allowed to gradually warm to room temperature over several hours. The reaction was quenched by the careful addition of H2O (50 mL), then most of the THF was removed on a rotatory evaporator. The residue was partitioned between dichloromethane (100 mL) and H2O (100 mL). The layers were separated and the aqueous later extracted a second time with dichloromethane (100 mL). The combined organic layers were washed with H2O (100 mL), dried (MgSO4), and concentrated to give the product as a clear oil.

1. additionwas added dropwise to the acid
2. additionOnce the addition
3. customThe reaction was quenched by the careful addition of H2O (50 mL)
4. custommost of the THF was removed on a rotatory evaporator
5. customThe residue was partitioned between dichloromethane (100 mL) and H2O (100 mL)
6. customThe layers were separated
7. extractionthe aqueous later extracted a second time with dichloromethane (100 mL)
8. washThe combined organic layers were washed with H2O (100 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated

ORD record

ord-2a309eaeb0d1480188ccd6c0c41f0e4e

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04918064