Potassium Phosphate, Tribasic → HCID 67052695, compound

HRID 1472115Notes

Reaction equation

HRID 1472115 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:3]=1.[CH3:17][PH:18](=[O:20])[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][P:18](=[O:20])([CH3:19])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67052709HCID 67052709, compoundHCID 178503022methylphosphonoylmethane

Product 1

HCID 67052695HCID 67052695, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirring solution of 4-bromo-1-nitro-2-(propan-2-ylsulfonyl)benzene (0.44 g, 1.6 mmol) and Dimethyl Phosphine oxide (0.15 g, 1.9 mmol) in 1 mL of DMF, was added Potassium Phosphate (0.37 g, 1.8 mmol), Pd(OAc)2 (18 mg, 0.08 mmol), Xantphos (55 mg, 0.10 mmol). The reaction mixture was stirred at 110 degrees C overnight. The reaction mixture was cooled to room temperature and filtered through celite. The desired product was isolated through prep-HPLC to yield a brownish yellow solid (0.24 g, 55% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-0e9a2671960b48a2b4c55d34fd5079f9
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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