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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1965573Generated: October 30, 2026

2-(Bromomethyl)-5-(trifluoromethyl)furan → 7'-chloro-1'-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one

https://huagongshe.com/reaction/1965573

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-(Bromomethyl)-5-(trifluoromethyl)furanHCID 2794605—
Reactant5-(Chloromethyl)-2-methoxypyrimidineHCID 21698173—
Reactant5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 59263354—
Reactant7'-chloro-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-oneHCID 59352100—
Product7'-chloro-1'-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 59352420—

Reaction Steps

Following the procedure as described in EXAMPLE 5 and making non-critical variations using 7′-chloro-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, and 2-(bromomethyl)-5-(trifluoromethyl)furan to replace 5-(chloromethyl)-2-methoxypyrimidine, 7′-chloro-1′-((5-(trifluoromethyl)furan-2-yl)methyl)-5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3′-indolin]-2′-one was obtained (30%) as a colorless solid: mp 210-211° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ7.34-7.31 (m, 1H), 7.21-7.16 (m, 2H), 7.10-7.05 (m, 1H), 6.67-6.65 (m, 1H), 6.49 (s, 1H), 6.43 (s, 1H), 5.34 (s, 2H), 4.85 (d, J=9.6 Hz, 1H), 4.74 (d, J=9.6 Hz, 1H), 4.57-4.48 (m, 2H), 2.94 (t, J=3.0 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ177.4, 161.2, 160.4, 154.1, 139.4, 138.9, 137.2, 135.4, 130.5, 124.6, 122.8, 120.6, 120.1, 119.9, 118.7, 117.1, 114.3, 114.2, 108.7, 92.4, 79.8, 72.0, 56.6, 28.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08415370B2
Source datasetuspto-grants-2013_04
ORD IDord-39f3110c4ecd4b67935cfb4b13256ace
Source noteuspto-grants-2013_04