Dimethyl Sulfoxide → HCID 86693488, compound

HRID 575432Notes

Reaction equation

HRID 575432 reaction equation
Br[CH:2]1[C:8]2[CH:9]=[C:10]([I:14])[C:11]([F:13])=[CH:12][C:7]=2[CH:6]2[CH2:15][CH:4]([CH2:5]2)[C:3]1=[O:16].CS(C)=[O:19]>>[F:13][C:11]1[C:10]([I:14])=[CH:9][C:8]2[C:2](=[O:19])[C:3](=[O:16])[CH:4]3[CH2:15][CH:6]([C:7]=2[CH:12]=1)[CH2:5]3

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 86693489HCID 86693489, compound

Product 1

HCID 86693488HCID 86693488, compound

Procedure

A solution of crude 9-bromo-3-fluoro-2-iodo-6,7-dihydro-5H-5,7-methanobenzo[7]annulen-8(9H)-one (1.400 g at 87% purity LCMS-UV215) in dimethylsulfoxide (15 mL) was warmed to 80° C. for 1 hr under an atmosphere of nitrogen. Evaporation in vacuo furnished the crude title compound (2.855 g) containing residual DMSO as a golden-brown oil which was carried through to the next synthetic step without further purification: 1H NMR (500 MHz, CDCl3) δ 2.25-2.30 (m, 2H), 3.12-3.18 (m, 2H), 3.48-3.51 (m, 1H), 3.61-3.65 (m, 1H), 6.94 (d, J=8.2 Hz, 1H), 8.55 (d, J=6.6 Hz, 1H).

Workup

  1. customEvaporation in vacuo

Sources & evidence

ORD record
ord-2e687fadc2f64d4992bad106e22b5ff4
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…