Potassium Phosphate, Tribasic → HCID 57706456, compound

HRID 1662356Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1.CN(C=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12]

Participants

Conditions

Temperature: 40 °C

Procedure

A screw-cap vial was charged with 4-chloro-3-(trifluoromethoxy)benzaldehyde (available from Alfa Aesar, Avocado, Lancaster) (0.184 g, 0.82 mmol), 2-fluoro-5-methoxyphenylboronic acid (available from Aldrich) (0.278 g, 1.64 mmol), potassium phosphate (0.522 g, 2.46 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.101 g, 0.25 mmol), palladium(II) acetate (0.018 g, 0.082 mmol), and 5:1 THF/DMF (3.6 mL). The mixture was stirred overnight at 40° C., cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (0-10% EtOAc/hexane) to afford 46.1 (165 mg, 64%) as a colorless oil.

Workup

temperaturecooled to room temperature
washwashed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was chromatographed on silica gel (0-10% EtOAc/hexane)

Sources & evidence

ORD record: ord-3aee63ab0296439ba3827ba918c2b969
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

Loading…