Dimethyl Sulfoxide → HCID 86693483, compound

HRID 575428Notes

Reaction equation

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

Participants

Reactant 2

HCID 679Dimethyl Sulfoxide

HCID 86693484HCID 86693484, compound

Product 1

HCID 86693483HCID 86693483, compoundYield 72%

Procedure

A solution of 2,9-dibromo-3-fluoro-6,7-dihydro-5H-5,7-methanobenzo[7]annulen-8(9H)-one (1.04 g at 65% purity LC-UV215) in dimethylsulfoxide (15 mL) was warmed to 80° C. for 1 hr. Evaporation of the reaction mixture (high vacuum distillation) furnished the crude title compound (0.87 g at 72% purity LC-UV215) as a golden-brown syrup which was carried through to the next synthetic step without 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); M+1=305/307.

Workup

customEvaporation of the reaction mixture (high vacuum distillation)

Sources & evidence

ORD record: ord-8036a2c974cd4ebc82ee7f28ec89d6fa
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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