Water → Methyl 3-allylbenzoate

HRID 1510121Notes

Reaction equation

HRID 1510121 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:12]([Sn](CCCC)CCCC)[CH2:13][CH2:14]C.O>CN(C=O)C>[CH2:14]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 962WaterHCID 12070Methyl 3-bromobenzoateHCID 3032732Tributylstannanyl

Product 1

HCID 10559182Methyl 3-allylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-bromobenzoate (10.0 g, 46.5 mmol) in DMF (50 mL) was added ally tributyltin (23.1 g, 69.8 mmol) followed by tetrakis(triphenylphoshine) palladium(0) (1.08 g, 0.93 mmol). After stirring 80° C. overnight the reaction mixture was poured into H2O (500 mL), extracted with ethyl acetate (three times), dried over MgSO4 and concentrated under vacuum to afford the desired product.

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d62c07086d634a589149020cd79fbacc
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

Loading…