2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(Bicyclo[3.2.1]oct-2-en-2-yl)-3-methyl-benzoic acid methyl ester

HRID 1794011Notes

Reaction equation

HRID 1794011 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[CH2:34][CH:31]([CH2:32][CH:33]=1)[CH2:30][CH2:29]2)(=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[CH2:34][CH:31]([CH2:32][CH:33]=2)[CH2:30][CH2:29]3)=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 22219695Bicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Product 1

HCID 696525234-(Bicyclo[3.2.1]oct-2-en-2-yl)-3-methyl-benzoic acid methyl esterYield 57.6%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (0.300 g, 1.09 mmol) and bicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (0.336 g, 1.31 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with 5% ethyl acetate in hexane, afforded the title compound (0.161 g) as a light yellow oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f265cd4820244680a6112c9a937e0b60
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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