Methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate → Methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate

HRID 337649Notes

Reaction equation

HRID 337649 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](/[CH:13]=[CH:14]/[CH2:15][O:16][CH3:17])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir].ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 67062162Methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate

Product 1

HCID 66895990Methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 5702647(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.2 M) solution of methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate (1 eq.) from the previous step was added Crabtree's catalyst (0.01 eq.). The resulting orange red solution was bubbled with hydrogen for 10 min to activate the catalyst and then stirred at RT under a static balloon atmosphere of hydrogen for 3 h. Finally, removal of the volatiles in vacuo afforded the crude title compound as a yellow oil.

Workup

  1. customThe resulting orange red solution was bubbled with hydrogen for 10 min
  2. customFinally, removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-e8d6ee2315324a5fbde85c8cdfcb8ff8
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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