Benzyl4-iodobenzoate

To 4-iodobenzoic acid (15.62g, 63mmol, 1.05eq) in dry DMF (6vol, 90ml) was added potassium carbonate (8.7g, 63mmol, 1.05eq) and the suspension was stirred for 10min. Benzyl bromide (10.25g, 7.13ml, 60mmol, 1 eq) was then added over ca. 1 min. and the resulting suspension was stirred at room temperature under nitrogen for 6.25hr. The mixture was partitioned between ether (200ml) and water (200ml). The aqueous phase was extracted with more ether, then the combined organics were washed with water, aqueous lithium chloride, brine, dried and then evaporated to give the title compound as a white crystalline solid after leaving under vacuum (18.38g, 86percent). LCMS; tRET = 3.81 min, 70percent ES +ve 376, 356 (+ artefact 1.48min. 28percent).

Molecular Weight:338.14
XLogP3:4.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:337.98038
Monoisotopic Mass:337.98038
Topological Polar Surface Area:26.3
Heavy Atom Count:17
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes