3-Bromobenzonitrile → HCID 19102561, compound

HRID 1198553Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1/[CH:25]=[CH:26]/[C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=[O:31].[Cl-].[NH4+]>CCCCCC.O1CCCC1.CCOCC>[OH:31][CH:30]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])[C:29]1[CH:32]=[CH:33][CH:34]=[C:27](/[CH:26]=[CH:25]/[C:16]2[CH:17]=[CH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]=2)[CH:28]=1

Participants

Conditions

Temperature: -100 °C

Procedure

2.5M n-Butyl lithium solution in hexane (2.6 ml) was added dropwise to a stirred solution of 3-bromobenzonitrile (1.2 g, 6.56 mmol) in tetrahydrofuran (20 ml) and ether (20 ml) at -100° to -110° C. under nitrogen. The yellow solution was stirred at -100° C. for 5 minutes, then a solution of 3-[2(E)-(quinolin-2-yl)ethenyl]benzaldehyde (1.7 g, 6.56 mmol) in tetrahydrofuran (7 ml) was added. The dark brown solution was allowed to warm to room temperature, poured onto saturated ammonium chloride solution and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:2) to give a pale yellow solid.

Workup

temperatureto warm to room temperature
extractionextracted with ethyl acetate
customThe extract was dried
customevaporated
customthe residue was chromatographed on silica in ethyl acetate-hexane (1:2)
customto give a pale yellow solid

Sources & evidence

ORD record: ord-f69f63cca7494800852d6c5dbf79cecd
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281593

Reaction notes

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