2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-3-methyl-benzoic acid methyl ester

HRID 1794013Notes

Reaction equation

HRID 1794013 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[C:6]([CH3:19])[CH:5]=1.FC(F)(F)S(O[C:27]1[CH:28]2[CH2:33][CH:30]([CH2:31][CH:32]=1)[C:29]2([CH3:35])[CH3:34])(=O)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:27]2[CH:28]3[CH2:33][CH:30]([CH2:31][CH:32]=2)[C:29]3([CH3:35])[CH3:34])=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 222196936,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate

Product 1

HCID 696525154-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-3-methyl-benzoic acid methyl esterYield 69.5%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (1.00 g, 3.62 mmol) and 6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl trifluoromethanesulfonate (1.17 g, 4.34 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane, afforded the title compound (0.680 g) as a light yellow oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3e0bd9e391ec4410a11aee9176336aed
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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