1-Bromo-3,5-dimethoxybenzene → 3-(3,5-Dimethoxyphenyl)-1-propene

HRID 602069

Reaction equation

HRID 602069 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH2:12](B1OC(C)(C)C(C)(C)O1)[CH:13]=[CH2:14]>[Pd]>[CH2:14]([C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1)[CH:13]=[CH2:12]

Participants

4

Reactant 2

HCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane

Product 1

HCID 5248743-(3,5-Dimethoxyphenyl)-1-propene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The Pd-catalyzed cross-coupling reaction of 5-Bromo-1,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl-1,3-dimethoxybenzene 1 in excellent yield. AlI3 will be used for demethylating 5-Allyl-1,3-dimethoxybenzene with CS2 as solvent to produce 5-allylresorcinol 2. The bis(phosphinite) PCP ligands 3 will be obtained by diphosphorylation of 5-allylresorcinol 2 with the respective chlorophosphine and sodium hydride as a base. Iridium complexes 4 will be obtained from reaction of the respective PCP ligands 3 with [Ir(COD)Cl]2 or [Ir(COE)2Cl]2. Hydrosilylation of complexes 4 will produce the hydrosilylated complexes 5. Reaction of complexes 5 with silica gel will afford the Si2O-supported Ir complexes 6. To date, 5-allyl-1,3-dimethoxybenzene 1 has been prepared in 92% yield.

Sources & evidence

ORD record
ord-376ca710da7348ff836753aa74e52718
Source dataset
uspto-grants-2011_03
Patent number
US07902417B2

Linked notes

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