1,3-Dimethoxybenzene → 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

To a solution of 1,3-dimethoxybenzene (2 ml, 15.30 mmol) in anhydrous THF (35 ml) at 0° C., nBuLi (6.2 ml, 15.50 mmol) is added to the dropping funnel for 5 min. The reaction medium is stirred at room temperature for 3.5 h, then 2-bromochlorobenzene (1.6 ml, 13.70 mmol) is added by syringe, dropwise, at 0° C., for 30 min. After 15 min of stirring, the reaction medium is cooled to −78° C. and nBuLi (6.20 ml, 15.50 mmol) is added to the dropping funnel dropwise for 5 min. After 30 min, chlorodicyclohexylphosphine (3.03 ml, 13.70 mmol) is added. The reaction medium is maintained at −78° C. for 1 h, under rapid stirring (mechanical stirring). After returning to room temperature, the precipitate obtained is filtered on a fritted disc containing silica topped with a layer of cellulose acetate, with 600 ml ethyl acetate. The solvents are evaporated with a rotary evaporator, and the orange oil obtained is recrystallized in acetone to obtain S-Phos ligand in the form of white crystals with a yield of 36% (1.22 g, 2.97 mmol).

1. waitdropwise, at 0° C., for 30 min
2. stirringAfter 15 min of stirring
3. temperaturethe reaction medium is cooled to −78° C.
4. waitAfter 30 min
5. temperatureThe reaction medium is maintained at −78° C. for 1 h
6. stirringunder rapid stirring
7. stirring(mechanical stirring)
8. customAfter returning to room temperature
9. customthe precipitate obtained
10. filtrationis filtered on a fritted disc
11. additioncontaining silica
12. customThe solvents are evaporated with a rotary evaporator
13. customthe orange oil obtained
14. customis recrystallized in acetone

ORD record

ord-f91a150793bc4f2fafdf752a48cbf6af

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563548B2