Allyltributylstannane → 2-Allyl-5-methoxy-benzoic acid methyl ester

HRID 2261780Notes

Reaction equation

HRID 2261780 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1Br.[CH2:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=[CH2:16]>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 2776849Methyl 2-bromo-5-methoxybenzoate

Product 1

HCID 574433022-Allyl-5-methoxy-benzoic acid methyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

To an ambient temperature solution of 2-Bromo-5-methoxy-benzoic acid methyl ester (750 mg, 3.02 mmol) in benzene (2 mL) are added allyltri-n-butyl tin (1.16 mL, 3.73 mmol) and tetrakis(triphenylphosphine)palladium (0) (174 mg, 0.157 mmol, 5 mol %). The reaction mixture is heated in a sealed tube to 100° C. After 3 h, the reaction is concentrated under reduced pressure and the residue is chromatographed (0% to 10% EtOAc/Hex) to yield the title compound (451 mg, 73%). 1H NMR (400 MHz, CDCl3) δ 7.40 (d, 1H, J=2.6 Hz), 7.18 (d, 1H, J=8.4 Hz), 7.00 (dd, 1H, J=8.6, 2.9 Hz), 6.04-5.93 (m, 1H), 5.03-4.94 (m, 2H), 3.88 (s, 3H), 3.82 (s, 3H), 3.70-3.65 (m, 2H).

Workup

  1. concentrationthe reaction is concentrated under reduced pressure
  2. customthe residue is chromatographed (0% to 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-ba9685342456461190719ac214ae83fd
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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