Hydrochloric Acid → HCID 59642515, compound

HRID 15713

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.CCCCCC.[C:25]1([CH:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:33](=O)[O:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O1CCCC1>[C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:33]1[O:32][C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:40]2[C:35]=1[CH:36]=[CH:37][CH:38]=[CH:39]2

Participants

Conditions

Temperature: -50 °C

Procedure

In Ar, 3.9 g (1.68E-2 mol) of o-bromobiphenyl was dissolved in 30 cm3 of tetrahydrofuran (THF) at −50° C. To the solution was added 10 cM3 of a nBuLi hexane solution (1.5 mol/l). After 2 hours, 3 g (1.4E-2 mol) of 3-phenylphthalide was added to the solution while it was kept cooled at −50° C. After 2 hours, the reaction solution was allowed to resume room temperature, and 10 cm3 of a 35% aqueous hydrochloric acid was added thereto. After 1 hour, toluene extraction was carried out using a separatory funnel, followed by thorough washing with distilled water. After the toluene solution was concentrated, the end product was isolated by silica gel chromatography (developer, toluene:hexane=1:4). There was obtained 4 g (80%) of a yellow viscous substance emitting bluish green fluorescence.

Workup

waitAfter 2 hours
customto resume room temperature
waitAfter 1 hour
extractiontoluene extraction
washby thorough washing with distilled water
concentrationAfter the toluene solution was concentrated
customthe end product was isolated by silica gel chromatography (developer, toluene:hexane=1:4)
customThere was obtained 4 g (80%) of a yellow viscous substance

Sources & evidence

ORD record: ord-aff8c3652e3f40dfb2b6af6c85dd89ca
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732652B2

Linked notes

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